AU2002358053B2 - [1.2]-oxazin-3,5-diones - Google Patents
[1.2]-oxazin-3,5-diones Download PDFInfo
- Publication number
- AU2002358053B2 AU2002358053B2 AU2002358053A AU2002358053A AU2002358053B2 AU 2002358053 B2 AU2002358053 B2 AU 2002358053B2 AU 2002358053 A AU2002358053 A AU 2002358053A AU 2002358053 A AU2002358053 A AU 2002358053A AU 2002358053 B2 AU2002358053 B2 AU 2002358053B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- alkoxy
- optionally
- chlorine
- methyl
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 claims description 260
- -1 polyalkoxyalkyl Chemical group 0.000 claims description 197
- 239000001257 hydrogen Substances 0.000 claims description 170
- 229910052739 hydrogen Inorganic materials 0.000 claims description 170
- 239000000460 chlorine Substances 0.000 claims description 150
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 149
- 229910052801 chlorine Inorganic materials 0.000 claims description 138
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 131
- 150000002431 hydrogen Chemical class 0.000 claims description 130
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 101
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 101
- 229910052794 bromium Inorganic materials 0.000 claims description 101
- 239000011737 fluorine Substances 0.000 claims description 89
- 229910052731 fluorine Inorganic materials 0.000 claims description 89
- 238000000034 method Methods 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 72
- 150000002367 halogens Chemical class 0.000 claims description 72
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 68
- 230000008569 process Effects 0.000 claims description 67
- 125000001153 fluoro group Chemical group F* 0.000 claims description 66
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 48
- 239000001301 oxygen Substances 0.000 claims description 48
- 229910052760 oxygen Inorganic materials 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 239000003085 diluting agent Substances 0.000 claims description 46
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 45
- 239000005864 Sulphur Substances 0.000 claims description 45
- 239000011230 binding agent Substances 0.000 claims description 43
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 26
- 125000001188 haloalkyl group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 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 claims description 23
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
- 239000004009 herbicide Substances 0.000 claims description 20
- 241000607479 Yersinia pestis Species 0.000 claims description 19
- 241000233866 Fungi Species 0.000 claims description 18
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 15
- 241001465754 Metazoa Species 0.000 claims description 14
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 239000004606 Fillers/Extenders Substances 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910021645 metal ion Inorganic materials 0.000 claims description 8
- 230000003641 microbiacidal effect Effects 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000000575 pesticide Substances 0.000 claims description 8
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229940124561 microbicide Drugs 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical class 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 150000007970 thio esters Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino 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
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000005108 alkenylthio 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
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 150000002736 metal compounds 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 89
- 239000000203 mixture Substances 0.000 description 82
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
- 239000002904 solvent Substances 0.000 description 43
- 238000002360 preparation method Methods 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
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- 238000012360 testing method Methods 0.000 description 18
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- 230000000694 effects Effects 0.000 description 16
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- 108010050014 systemin Proteins 0.000 description 1
- AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 1
- 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
- 229960005199 tetramethrin Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 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
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 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
- 238000012546 transfer Methods 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-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
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-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
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 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
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10160007A DE10160007A1 (de) | 2001-12-06 | 2001-12-06 | [1.2]-Oxazin-3,5-dione |
| DE10160007.0 | 2001-12-06 | ||
| PCT/EP2002/013382 WO2003048138A1 (de) | 2001-12-06 | 2002-11-27 | [1.2]-oxazin-3,5-dione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002358053A1 AU2002358053A1 (en) | 2003-06-17 |
| AU2002358053B2 true AU2002358053B2 (en) | 2008-05-08 |
Family
ID=7708295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002358053A Ceased AU2002358053B2 (en) | 2001-12-06 | 2002-11-27 | [1.2]-oxazin-3,5-diones |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7183238B2 (https=) |
| EP (1) | EP1456185A1 (https=) |
| JP (1) | JP4542340B2 (https=) |
| KR (1) | KR100861483B1 (https=) |
| CN (1) | CN100506806C (https=) |
| AU (1) | AU2002358053B2 (https=) |
| BR (1) | BR0214759A (https=) |
| CA (1) | CA2469191C (https=) |
| DE (1) | DE10160007A1 (https=) |
| MX (1) | MXPA04005371A (https=) |
| PL (1) | PL370715A1 (https=) |
| RU (1) | RU2004120559A (https=) |
| WO (1) | WO2003048138A1 (https=) |
| ZA (1) | ZA200404286B (https=) |
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 |
| 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 |
| PL2222657T3 (pl) | 2007-12-13 | 2013-03-29 | Syngenta Ltd | Piranodiony, tiopiranodiony i cykloheksanotriony o właściwościach chwastobójczych |
| GB0821010D0 (en) * | 2008-11-17 | 2008-12-24 | Univ Warwick | Plant development control composition |
| CN102348684B (zh) * | 2009-03-11 | 2014-11-12 | 拜尔农作物科学股份公司 | 被卤代烷基亚甲基氧基苯基取代的酮烯醇 |
| JP2013514343A (ja) * | 2009-12-17 | 2013-04-25 | シンジェンタ リミテッド | 除草剤活性ピランジオンを含んでなる除草剤組成物、および除草剤活性ピランジオンの使用法 |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| EP2742030B1 (de) | 2011-08-11 | 2016-07-27 | Bayer Intellectual Property GmbH | 1,2,4-triazolyl-substituierte ketoenole zum einsatz im pflanzenschutz |
| KR102030337B1 (ko) | 2012-01-26 | 2019-10-10 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 어류 기생충 방제용의 페닐-치환된 케토에놀 |
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 |
| CA2072134A1 (en) | 1990-10-25 | 1992-04-26 | Shy-Fuh Lee | Heterocyclic dione derivatives as pesticides and plant growth regulators |
| US5358924A (en) * | 1991-03-21 | 1994-10-25 | Bayer Aktiengesellschaft | 3-hydroxy-4-aryl-5-oxo-pyrozoline derivatives, compositions and use |
| DE4109208A1 (de) * | 1991-03-21 | 1992-09-24 | Bayer Ag | 3-hydroxy-4-aryl-5-oxo-pyrazolin-derivate |
| 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 |
| ES2190786T3 (es) | 1994-04-05 | 2003-08-16 | Bayer Cropscience Ag | 1-h-3-aril-pirrolidin-2,4-dionas alcoxi-alquil-substituidas como herbicidas y pesticidas. |
| US6358887B1 (en) | 1995-02-13 | 2002-03-19 | Bayer Aktiengesellschaft | 2-Phenyl-substituted heterocyclic 1,3-ketonols as herbicides and pesticides |
| CN1131209C (zh) | 1995-05-09 | 2003-12-17 | 拜尔公司 | 可用作杀虫剂和除草剂的烷基－二卤代苯基取代的酮烯醇 |
| GB9510459D0 (en) | 1995-05-24 | 1995-07-19 | Zeneca Ltd | Bicyclic amines |
| MX9710373A (es) | 1995-06-28 | 1998-07-31 | Bayer Ag | Fenilcetoenoles 2,4,5-trisubstituidos para el empleo como pesticidas y herbicidas. |
| CN1152860C (zh) | 1995-06-30 | 2004-06-09 | 拜尔公司 | 二烷基-卤代苯基取代的酮-烯醇 |
| CN1215390A (zh) | 1996-04-02 | 1999-04-28 | 拜尔公司 | 取代的苯基酮烯醇杀虫剂及除草剂 |
| WO1997043286A1 (en) | 1996-05-13 | 1997-11-20 | Zeneca Limited | Bicyclic amines as insecticides |
| ES2275796T3 (es) | 1996-08-05 | 2007-06-16 | Bayer Cropscience Ag | Fenilcetoenoles 2- y 2,5-substituidos. |
| WO1998025924A1 (en) | 1996-11-26 | 1998-06-18 | Zeneca Limited | 8-azabicyclo[3.2.1]octane-, 8-azabicyclo[3.2.1]oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane- and 9-aza-3-thiabicyclo[3.3.1]nonane derivatives, their preparation and their use as insecticides |
| 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 |
| RU2269537C2 (ru) * | 1999-09-07 | 2006-02-10 | Зингента Партисипейшнс Аг | Фенилзамещенные гетероциклические 1,3-кетоенолы, способ их получения, гербицидное средство на их основе и способ борьбы с ростом нежелательной растительности |
-
2001
- 2001-12-06 DE DE10160007A patent/DE10160007A1/de not_active Withdrawn
-
2002
- 2002-11-27 BR BR0214759-9A patent/BR0214759A/pt not_active Application Discontinuation
- 2002-11-27 WO PCT/EP2002/013382 patent/WO2003048138A1/de not_active Ceased
- 2002-11-27 CA CA2469191A patent/CA2469191C/en not_active Expired - Fee Related
- 2002-11-27 AU AU2002358053A patent/AU2002358053B2/en not_active Ceased
- 2002-11-27 US US10/497,479 patent/US7183238B2/en not_active Expired - Fee Related
- 2002-11-27 MX MXPA04005371A patent/MXPA04005371A/es active IP Right Grant
- 2002-11-27 KR KR1020047007909A patent/KR100861483B1/ko not_active Expired - Fee Related
- 2002-11-27 PL PL02370715A patent/PL370715A1/xx unknown
- 2002-11-27 RU RU2004120559/04A patent/RU2004120559A/ru not_active Application Discontinuation
- 2002-11-27 CN CN02827658.2A patent/CN100506806C/zh not_active Expired - Fee Related
- 2002-11-27 EP EP02791728A patent/EP1456185A1/de not_active Withdrawn
- 2002-11-27 JP JP2003549330A patent/JP4542340B2/ja not_active Expired - Fee Related
-
2004
- 2004-06-01 ZA ZA200404286A patent/ZA200404286B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002358053A1 (en) | 2003-06-17 |
| BR0214759A (pt) | 2004-12-14 |
| JP2005518370A (ja) | 2005-06-23 |
| JP4542340B2 (ja) | 2010-09-15 |
| EP1456185A1 (de) | 2004-09-15 |
| US20050070707A1 (en) | 2005-03-31 |
| KR20050044597A (ko) | 2005-05-12 |
| CN100506806C (zh) | 2009-07-01 |
| WO2003048138A1 (de) | 2003-06-12 |
| CA2469191C (en) | 2012-07-10 |
| RU2004120559A (ru) | 2006-01-10 |
| ZA200404286B (en) | 2005-06-01 |
| DE10160007A1 (de) | 2003-06-18 |
| MXPA04005371A (es) | 2004-09-27 |
| US7183238B2 (en) | 2007-02-27 |
| PL370715A1 (en) | 2005-05-30 |
| CN1617860A (zh) | 2005-05-18 |
| KR100861483B1 (ko) | 2008-10-02 |
| CA2469191A1 (en) | 2003-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |