DE10160007A1 - [1.2]-Oxazin-3,5-dione - Google Patents
[1.2]-Oxazin-3,5-dioneInfo
- Publication number
- DE10160007A1 DE10160007A1 DE10160007A DE10160007A DE10160007A1 DE 10160007 A1 DE10160007 A1 DE 10160007A1 DE 10160007 A DE10160007 A DE 10160007A DE 10160007 A DE10160007 A DE 10160007A DE 10160007 A1 DE10160007 A1 DE 10160007A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- alkyl
- given above
- spp
- 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.)
- Withdrawn
Links
- KDZFOYZCCXIDJJ-UHFFFAOYSA-N oxazinane-3,5-dione Chemical compound O=C1CONC(=O)C1 KDZFOYZCCXIDJJ-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 72
- 239000004009 herbicide Substances 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 239000000575 pesticide Substances 0.000 claims abstract description 8
- 230000003641 microbiacidal effect Effects 0.000 claims abstract description 7
- 229940124561 microbicide Drugs 0.000 claims abstract description 6
- -1 polyalkoxyalkyl Chemical group 0.000 claims description 142
- 150000001875 compounds Chemical class 0.000 claims description 137
- 230000008569 process Effects 0.000 claims description 56
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 150000002367 halogens Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 239000003085 diluting agent Substances 0.000 claims description 45
- 150000002431 hydrogen Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 43
- 239000011230 binding agent Substances 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 29
- 239000011593 sulfur Substances 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 241000607479 Yersinia pestis Species 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 239000004606 Fillers/Extenders Substances 0.000 claims description 8
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 8
- 229920006395 saturated elastomer Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical class NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims description 2
- LRYSUGTXBIPBGB-UHFFFAOYSA-N chloromethanedithioic acid Chemical class SC(Cl)=S LRYSUGTXBIPBGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 2
- 230000002363 herbicidal effect Effects 0.000 abstract description 5
- 239000002855 microbicide agent Substances 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 86
- 239000000203 mixture Substances 0.000 description 66
- 239000004480 active ingredient Substances 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 55
- 239000000460 chlorine Substances 0.000 description 55
- 229910052801 chlorine Inorganic materials 0.000 description 53
- 239000011737 fluorine Substances 0.000 description 47
- 229910052731 fluorine Inorganic materials 0.000 description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 43
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 41
- 229910052794 bromium Inorganic materials 0.000 description 41
- 239000002904 solvent Substances 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000000126 substance Substances 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000003995 emulsifying agent Substances 0.000 description 27
- 125000001153 fluoro group Chemical group F* 0.000 description 26
- 238000009472 formulation Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 20
- 239000000463 material Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 239000008187 granular material Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 239000002917 insecticide Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 150000002170 ethers Chemical class 0.000 description 14
- 239000000417 fungicide Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 239000002023 wood Substances 0.000 description 14
- 230000001965 increasing effect Effects 0.000 description 13
- 239000002689 soil Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 241000238631 Hexapoda Species 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 241000233866 Fungi Species 0.000 description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 10
- 239000000969 carrier Substances 0.000 description 10
- 244000005700 microbiome Species 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 239000011877 solvent mixture Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 241000219146 Gossypium Species 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000002877 alkyl aryl group Chemical group 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 229920000151 polyglycol Polymers 0.000 description 9
- 239000010695 polyglycol Substances 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 241000238876 Acari Species 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 8
- 235000010469 Glycine max Nutrition 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 239000011435 rock Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- 239000006072 paste Substances 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 230000000895 acaricidal effect Effects 0.000 description 6
- 239000000642 acaricide Substances 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 230000003373 anti-fouling effect Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 230000009261 transgenic effect Effects 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 5
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 5
- 239000005877 Alpha-Cypermethrin Substances 0.000 description 5
- 241000193388 Bacillus thuringiensis Species 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 5
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 241001177134 Lyctus Species 0.000 description 5
- 241000208125 Nicotiana Species 0.000 description 5
- 240000006394 Sorghum bicolor Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 229940097012 bacillus thuringiensis Drugs 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 230000007123 defense Effects 0.000 description 5
- 229960003887 dichlorophen Drugs 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000005645 nematicide Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 150000003457 sulfones Chemical class 0.000 description 5
- 150000003462 sulfoxides Chemical class 0.000 description 5
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- 239000008158 vegetable oil Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical class 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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- WJSXSXUHWBSPEP-UHFFFAOYSA-N pyridine;triphenylborane Chemical class C1=CC=NC=C1.C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 WJSXSXUHWBSPEP-UHFFFAOYSA-N 0.000 description 1
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
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- 238000012552 review Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
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- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- HOWHQWFXSLOJEF-MGZLOUMQSA-N systemin Chemical compound NCCCC[C@H](N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)OC(=O)[C@@H]1CCCN1C(=O)[C@H]1N(C(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]2N(CCC2)C(=O)[C@H]2N(CCC2)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)N)C(C)C)CCC1 HOWHQWFXSLOJEF-MGZLOUMQSA-N 0.000 description 1
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- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- WVZPYZMQQDNINJ-UHFFFAOYSA-N tributyl(butylstannyloxy)stannane Chemical class CCCC[SnH](CCCC)O[SnH](CCCC)CCCC WVZPYZMQQDNINJ-UHFFFAOYSA-N 0.000 description 1
- YDUBPEZBWPRJJL-UHFFFAOYSA-M tributyl-(4-chloro-2-phenylphenoxy)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)OC1=CC=C(Cl)C=C1C1=CC=CC=C1 YDUBPEZBWPRJJL-UHFFFAOYSA-M 0.000 description 1
- HFFZSMFXOBHQLV-UHFFFAOYSA-M tributylstannyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)CCCC HFFZSMFXOBHQLV-UHFFFAOYSA-M 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/02—1,2-Oxazines; Hydrogenated 1,2-oxazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10160007A DE10160007A1 (de) | 2001-12-06 | 2001-12-06 | [1.2]-Oxazin-3,5-dione |
| US10/497,479 US7183238B2 (en) | 2001-12-06 | 2002-11-27 | [1,2]-oxazine-3,5-diones |
| AU2002358053A AU2002358053B2 (en) | 2001-12-06 | 2002-11-27 | [1.2]-oxazin-3,5-diones |
| PL02370715A PL370715A1 (en) | 2001-12-06 | 2002-11-27 | [1.2]-oxazin-3,5-diones |
| CN02827658.2A CN100506806C (zh) | 2001-12-06 | 2002-11-27 | [1,2]-嗪-3,5-二酮类化合物 |
| RU2004120559/04A RU2004120559A (ru) | 2001-12-06 | 2002-11-27 | (1,2)-оксазин-3,5-дионы |
| BR0214759-9A BR0214759A (pt) | 2001-12-06 | 2002-11-27 | [1,2]-oxazin-3,5-dionas |
| KR1020047007909A KR100861483B1 (ko) | 2001-12-06 | 2002-11-27 | [1,2]-옥사진-3,5-디온 |
| EP02791728A EP1456185A1 (de) | 2001-12-06 | 2002-11-27 | (1.2)-oxazin-3,5-dione |
| JP2003549330A JP4542340B2 (ja) | 2001-12-06 | 2002-11-27 | ［１，２］−オキサジン−３，５−ジオン類 |
| CA2469191A CA2469191C (en) | 2001-12-06 | 2002-11-27 | [1,2]-oxazine-3,5-diones |
| MXPA04005371A MXPA04005371A (es) | 2001-12-06 | 2002-11-27 | [1,2]-oxazin-3,5-dionas. |
| PCT/EP2002/013382 WO2003048138A1 (de) | 2001-12-06 | 2002-11-27 | [1.2]-oxazin-3,5-dione |
| ZA200404286A ZA200404286B (en) | 2001-12-06 | 2004-06-01 | [1.2]-oxazin-3,5-diones. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10160007A DE10160007A1 (de) | 2001-12-06 | 2001-12-06 | [1.2]-Oxazin-3,5-dione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10160007A1 true DE10160007A1 (de) | 2003-06-18 |
Family
ID=7708295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10160007A Withdrawn DE10160007A1 (de) | 2001-12-06 | 2001-12-06 | [1.2]-Oxazin-3,5-dione |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7183238B2 (enExample) |
| EP (1) | EP1456185A1 (enExample) |
| JP (1) | JP4542340B2 (enExample) |
| KR (1) | KR100861483B1 (enExample) |
| CN (1) | CN100506806C (enExample) |
| AU (1) | AU2002358053B2 (enExample) |
| BR (1) | BR0214759A (enExample) |
| CA (1) | CA2469191C (enExample) |
| DE (1) | DE10160007A1 (enExample) |
| MX (1) | MXPA04005371A (enExample) |
| PL (1) | PL370715A1 (enExample) |
| RU (1) | RU2004120559A (enExample) |
| WO (1) | WO2003048138A1 (enExample) |
| ZA (1) | ZA200404286B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004032421A1 (de) * | 2004-07-05 | 2006-01-26 | Bayer Cropscience Ag | Phenylsubstituierte [1.2]-Oxazin-3,5-dion-und Dihydropyron-Derivate |
| SA07280691B1 (ar) * | 2006-12-14 | 2010-11-02 | سينجنتا بارتسبيشنز ايه جي | مركبات جديدة من 4- باي فينيل- بيران -3،5-دايون وإستخدامها كمبيدات أعشاب |
| CO6170061A1 (es) * | 2007-12-13 | 2010-06-18 | Syngenta Participations Ag | Compuestos de pirandiona, tiopirandiona y ciclohexantriona utiles como herbicidas, procesos para su preparacion, intermediarios utiles en su preparacion, metodos para controlar hierbas y malezas en cultivos de plantas utiles utilizando dichos herbici |
| GB0821010D0 (en) | 2008-11-17 | 2008-12-24 | Univ Warwick | Plant development control composition |
| PL2406216T3 (pl) | 2009-03-11 | 2017-09-29 | Bayer Intellectual Property Gmbh | Ketoenole podstawione halogenoalkilometylenoksyfenylem |
| KR20120105514A (ko) * | 2009-12-17 | 2012-09-25 | 신젠타 리미티드 | 제초 활성인 피란디온을 포함하는 제초제 조성물 및 이의 사용 방법 |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| WO2013021044A1 (de) | 2011-08-11 | 2013-02-14 | Bayer Intellectual Property Gmbh | 1,2,4-triazolyl-substituierte ketoenole |
| AU2013211636B2 (en) | 2012-01-26 | 2016-09-29 | Bayer Intellectual Property Gmbh | Phenyl-substituted ketoenols for controlling fish parasites |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5336662A (en) * | 1989-04-25 | 1994-08-09 | Sandoz Ltd. | Heterocyclic diones as plant growth regulators |
| TR24452A (tr) * | 1989-04-25 | 1991-11-01 | Sandoz Ltd | Pestisidler ve bitki bueyueme duezenleyicileri olarak heterosiklik dionlar |
| KR927003554A (ko) * | 1990-10-25 | 1992-12-18 | 예안 크레이머 | 살충제 및 식물 생장 조절제로서의 헤테로 사이클계 디온 유도체 |
| DE4109208A1 (de) * | 1991-03-21 | 1992-09-24 | Bayer Ag | 3-hydroxy-4-aryl-5-oxo-pyrazolin-derivate |
| US5358924A (en) * | 1991-03-21 | 1994-10-25 | Bayer Aktiengesellschaft | 3-hydroxy-4-aryl-5-oxo-pyrozoline derivatives, compositions and use |
| EP0702670A1 (de) | 1993-06-07 | 1996-03-27 | Bayer Ag | Iodpropargylcarbamate und ihre verwendung als biozide im pflanzen- und materialschutz |
| DE4425617A1 (de) | 1994-01-28 | 1995-08-03 | Bayer Ag | 1-H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
| DE4431730A1 (de) | 1994-02-09 | 1995-08-10 | Bayer Ag | Substituierte 1H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
| AU2072695A (en) | 1994-04-05 | 1995-10-23 | Bayer Aktiengesellschaft | Alkoxy-alkyl-substituted 1-h-3-aryl-pyrrolidine-2,4-diones used as herbicides and pesticides |
| JP4036470B2 (ja) | 1995-02-13 | 2008-01-23 | バイエル・アクチエンゲゼルシヤフト | 除草剤および有害生物防除剤としての２−フェニル置換複素環式１，３−ケトエノール |
| MX9708597A (es) | 1995-05-09 | 1998-02-28 | Bayer Ag | Cetoenoles alquil-dihalogenofenil substituidos como pesticidas y herbicidas. |
| GB9510459D0 (en) | 1995-05-24 | 1995-07-19 | Zeneca Ltd | Bicyclic amines |
| US6110872A (en) | 1995-06-28 | 2000-08-29 | Bayer Aktiengesellschaft | 2,4,5-trisubstituted phenylketo-enols for use as pesticides and herbicides |
| HUP9802279A3 (en) | 1995-06-30 | 2001-05-28 | Bayer Ag | Dialkyl phenyl halide-substituted keto-enols for use as herbicides and pesticides |
| WO1997036868A1 (de) | 1996-04-02 | 1997-10-09 | Bayer Aktiengesellschaft | Substituierte phenylketoenole als schädlingsbekämpfungsmittel und herbizide |
| BR9708947A (pt) | 1996-05-13 | 1999-08-03 | Zeneca Ltd | Composto composição inseticida acaricida e nematicida método para combate e controle de pragas e processo para preparação de um composto |
| DK1277749T3 (da) | 1996-08-05 | 2007-01-29 | Bayer Cropscience Ag | 2- og 2,5-substituerede phenylketoenoler |
| TW370451B (en) | 1996-11-26 | 1999-09-21 | Zeneca Ltd | Bicyclic amine derivatives |
| GB9624611D0 (en) | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Bicyclic amine compounds |
| DE19808261A1 (de) | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| DE19813354A1 (de) | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| DE19818732A1 (de) | 1998-04-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| CN1272324C (zh) * | 1999-09-07 | 2006-08-30 | 辛根塔参与股份公司 | 新颖的除草剂 |
-
2001
- 2001-12-06 DE DE10160007A patent/DE10160007A1/de not_active Withdrawn
-
2002
- 2002-11-27 KR KR1020047007909A patent/KR100861483B1/ko not_active Expired - Fee Related
- 2002-11-27 US US10/497,479 patent/US7183238B2/en not_active Expired - Fee Related
- 2002-11-27 CA CA2469191A patent/CA2469191C/en not_active Expired - Fee Related
- 2002-11-27 MX MXPA04005371A patent/MXPA04005371A/es active IP Right Grant
- 2002-11-27 JP JP2003549330A patent/JP4542340B2/ja not_active Expired - Fee Related
- 2002-11-27 RU RU2004120559/04A patent/RU2004120559A/ru not_active Application Discontinuation
- 2002-11-27 BR BR0214759-9A patent/BR0214759A/pt not_active Application Discontinuation
- 2002-11-27 CN CN02827658.2A patent/CN100506806C/zh not_active Expired - Fee Related
- 2002-11-27 PL PL02370715A patent/PL370715A1/xx unknown
- 2002-11-27 EP EP02791728A patent/EP1456185A1/de not_active Withdrawn
- 2002-11-27 AU AU2002358053A patent/AU2002358053B2/en not_active Ceased
- 2002-11-27 WO PCT/EP2002/013382 patent/WO2003048138A1/de not_active Ceased
-
2004
- 2004-06-01 ZA ZA200404286A patent/ZA200404286B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002358053B2 (en) | 2008-05-08 |
| US20050070707A1 (en) | 2005-03-31 |
| AU2002358053A1 (en) | 2003-06-17 |
| MXPA04005371A (es) | 2004-09-27 |
| US7183238B2 (en) | 2007-02-27 |
| CN1617860A (zh) | 2005-05-18 |
| JP4542340B2 (ja) | 2010-09-15 |
| ZA200404286B (en) | 2005-06-01 |
| KR20050044597A (ko) | 2005-05-12 |
| RU2004120559A (ru) | 2006-01-10 |
| CA2469191A1 (en) | 2003-06-12 |
| PL370715A1 (en) | 2005-05-30 |
| WO2003048138A1 (de) | 2003-06-12 |
| EP1456185A1 (de) | 2004-09-15 |
| CA2469191C (en) | 2012-07-10 |
| KR100861483B1 (ko) | 2008-10-02 |
| CN100506806C (zh) | 2009-07-01 |
| BR0214759A (pt) | 2004-12-14 |
| JP2005518370A (ja) | 2005-06-23 |
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