CA2469191C - [1,2]-oxazine-3,5-diones - Google Patents
[1,2]-oxazine-3,5-diones Download PDFInfo
- Publication number
- CA2469191C CA2469191C CA2469191A CA2469191A CA2469191C CA 2469191 C CA2469191 C CA 2469191C CA 2469191 A CA2469191 A CA 2469191A CA 2469191 A CA2469191 A CA 2469191A CA 2469191 C CA2469191 C CA 2469191C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkoxy
- optionally
- methyl
- haloalkyl
- 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 - Fee Related
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- KDZFOYZCCXIDJJ-UHFFFAOYSA-N oxazinane-3,5-dione Chemical class O=C1CONC(=O)C1 KDZFOYZCCXIDJJ-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000004009 herbicide Substances 0.000 claims abstract description 19
- 230000003641 microbiacidal effect Effects 0.000 claims abstract description 7
- 239000000575 pesticide Substances 0.000 claims abstract description 7
- 229940124561 microbicide Drugs 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 253
- -1 cyano- Chemical class 0.000 claims description 185
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 176
- 229910052801 chlorine Inorganic materials 0.000 claims description 130
- 229910052739 hydrogen Inorganic materials 0.000 claims description 102
- 229910052794 bromium Inorganic materials 0.000 claims description 95
- 239000000203 mixture Substances 0.000 claims description 85
- 229910052731 fluorine Inorganic materials 0.000 claims description 79
- 125000005843 halogen group Chemical group 0.000 claims description 79
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 70
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 46
- 239000003085 diluting agent Substances 0.000 claims description 46
- 239000011230 binding agent Substances 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 33
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 31
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 24
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 15
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical class 0.000 claims description 12
- 241000607479 Yersinia pestis Species 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 11
- 241000233866 Fungi Species 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 10
- 239000004606 Fillers/Extenders Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000003356 phenylsulfanyl group Chemical class [*]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
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical class 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910021645 metal ion Inorganic materials 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 150000007970 thio esters Chemical class 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 125000003358 C2-C20 alkenyl group Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 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
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 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
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical compound NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 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
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 239000002855 microbicide agent Substances 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 75
- 230000008569 process Effects 0.000 abstract description 62
- 238000002360 preparation method Methods 0.000 abstract description 39
- 241000196324 Embryophyta Species 0.000 description 89
- 239000001257 hydrogen Substances 0.000 description 87
- 239000000460 chlorine Substances 0.000 description 85
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 77
- 150000002431 hydrogen Chemical class 0.000 description 73
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 57
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 55
- 239000011737 fluorine Substances 0.000 description 47
- 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
- 229910052736 halogen Inorganic materials 0.000 description 37
- 125000001153 fluoro group Chemical group F* 0.000 description 34
- 150000002367 halogens Chemical class 0.000 description 31
- 239000003921 oil Substances 0.000 description 31
- 235000019198 oils Nutrition 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000003995 emulsifying agent Substances 0.000 description 28
- 238000009472 formulation Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- 239000000126 substance Substances 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 24
- 239000005864 Sulphur Substances 0.000 description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 24
- 239000001301 oxygen Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000008187 granular material Substances 0.000 description 20
- 239000007858 starting material Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 240000008042 Zea mays Species 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000002689 soil Substances 0.000 description 16
- 150000002170 ethers Chemical class 0.000 description 15
- 239000002917 insecticide Substances 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 14
- 239000000417 fungicide Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 239000002023 wood Substances 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 13
- 235000009973 maize Nutrition 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 229910052708 sodium Inorganic materials 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
- 230000001965 increasing effect Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 230000003373 anti-fouling effect Effects 0.000 description 10
- 239000000969 carrier Substances 0.000 description 10
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 244000005700 microbiome Species 0.000 description 10
- 235000010755 mineral Nutrition 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000000839 emulsion Substances 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000002480 mineral oil Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229920000151 polyglycol Polymers 0.000 description 9
- 239000010695 polyglycol Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
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- 229920000742 Cotton Polymers 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
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- 244000068988 Glycine max Species 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000003086 colorant Substances 0.000 description 8
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- 239000010949 copper Substances 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 241000193388 Bacillus thuringiensis Species 0.000 description 7
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- 238000010626 work up procedure Methods 0.000 description 7
- 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 6
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
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- 150000001298 alcohols Chemical class 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
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- 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
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- 229910000104 sodium hydride Inorganic materials 0.000 description 6
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- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 5
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- 235000013399 edible fruits Nutrition 0.000 description 5
- 125000004438 haloalkoxy group Chemical group 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 238000003306 harvesting Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
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- 229910052700 potassium Inorganic materials 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
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
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- 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
- 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 |
|---|---|
| CA2469191A1 CA2469191A1 (en) | 2003-06-12 |
| CA2469191C true CA2469191C (en) | 2012-07-10 |
Family
ID=7708295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2469191A Expired - Fee Related CA2469191C (en) | 2001-12-06 | 2002-11-27 | [1,2]-oxazine-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 |
| AU2002358053B2 (en) | 2008-05-08 |
| KR20050044597A (ko) | 2005-05-12 |
| CN100506806C (zh) | 2009-07-01 |
| WO2003048138A1 (de) | 2003-06-12 |
| 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 |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20131127 |