TW200918539A - Novel herbicides - Google Patents
Novel herbicides Download PDFInfo
- Publication number
- TW200918539A TW200918539A TW097124068A TW97124068A TW200918539A TW 200918539 A TW200918539 A TW 200918539A TW 097124068 A TW097124068 A TW 097124068A TW 97124068 A TW97124068 A TW 97124068A TW 200918539 A TW200918539 A TW 200918539A
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- Prior art keywords
- group
- formula
- compound
- hydrogen
- alkyl
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- 239000004009 herbicide Substances 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 840
- 229910052739 hydrogen Inorganic materials 0.000 claims description 533
- 239000001257 hydrogen Substances 0.000 claims description 531
- 150000002431 hydrogen Chemical group 0.000 claims description 326
- -1 cyclopropylethyl n-propyl Chemical group 0.000 claims description 264
- 125000000217 alkyl group Chemical group 0.000 claims description 257
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 159
- 239000000203 mixture Substances 0.000 claims description 116
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 104
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 94
- 125000003545 alkoxy group Chemical group 0.000 claims description 91
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 88
- 229910052736 halogen Inorganic materials 0.000 claims description 80
- 239000002585 base Substances 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 125000001072 heteroaryl group Chemical group 0.000 claims description 77
- 150000002367 halogens Chemical group 0.000 claims description 76
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 64
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 43
- 125000001188 haloalkyl group Chemical group 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 40
- 125000000304 alkynyl group Chemical group 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 37
- 239000000460 chlorine Substances 0.000 claims description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 20
- 241000196324 Embryophyta Species 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 19
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 230000002363 herbicidal effect Effects 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 16
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 15
- 239000011593 sulfur Substances 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 14
- 150000002923 oximes Chemical class 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 8
- 244000025254 Cannabis sativa Species 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 229920002554 vinyl polymer Chemical group 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
- PNDKCRDVVKJPKG-WHERJAGFSA-N cenicriviroc Chemical compound C1=CC(OCCOCCCC)=CC=C1C1=CC=C(N(CC(C)C)CCC\C(=C/2)C(=O)NC=3C=CC(=CC=3)[S@@](=O)CC=3N(C=NC=3)CCC)C\2=C1 PNDKCRDVVKJPKG-WHERJAGFSA-N 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000004969 haloethyl group Chemical group 0.000 claims description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 2
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004354 sulfur functional group Chemical group 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004970 halomethyl group Chemical group 0.000 claims 2
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical group FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 239000003708 ampul Substances 0.000 claims 1
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000000879 imine group Chemical group 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 171
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 93
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 239000007789 gas Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 32
- 235000019439 ethyl acetate Nutrition 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- 239000004480 active ingredient Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 125000001309 chloro group Chemical group Cl* 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000003446 ligand Substances 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 239000000654 additive Substances 0.000 description 17
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 17
- 229910052763 palladium Inorganic materials 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 16
- 239000000499 gel Substances 0.000 description 15
- 239000000284 extract Substances 0.000 description 13
- 239000000052 vinegar Substances 0.000 description 13
- 235000021419 vinegar Nutrition 0.000 description 13
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910052707 ruthenium Inorganic materials 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 11
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- 125000005843 halogen group Chemical group 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 11
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- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 10
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- 229910052744 lithium Inorganic materials 0.000 description 9
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 8
- 101150041968 CDC13 gene Proteins 0.000 description 8
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
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- 150000003973 alkyl amines Chemical class 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- 239000002562 thickening agent Substances 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-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
- 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
- 230000009466 transformation Effects 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- NYHDARUOKPETFK-UHFFFAOYSA-K triacetyloxylead Chemical compound CC(=O)O[Pb](OC(C)=O)OC(C)=O NYHDARUOKPETFK-UHFFFAOYSA-K 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 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
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- YGRHYJIWZFEDBT-UHFFFAOYSA-N tridecylaluminum Chemical compound CCCCCCCCCCCCC[Al] YGRHYJIWZFEDBT-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- JPJIEXKLJOWQQK-UHFFFAOYSA-K trifluoromethanesulfonate;yttrium(3+) Chemical compound [Y+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JPJIEXKLJOWQQK-UHFFFAOYSA-K 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
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0715576.5A GB0715576D0 (en) | 2007-08-09 | 2007-08-09 | Novel herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200918539A true TW200918539A (en) | 2009-05-01 |
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ID=38543340
Family Applications (1)
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| TW097124068A TW200918539A (en) | 2007-08-09 | 2008-06-27 | Novel herbicides |
Country Status (28)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0715454D0 (en) | 2007-08-08 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| GB0715576D0 (en) | 2007-08-09 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| GB0717082D0 (en) * | 2007-09-03 | 2007-10-10 | Syngenta Ltd | Novel herbicides |
| US8367873B2 (en) | 2008-10-10 | 2013-02-05 | Bayer Cropscience Ag | Phenyl-substituted bicyclooctane-1,3-dione derivatives |
| GB0822834D0 (en) | 2008-12-15 | 2009-01-21 | Syngenta Ltd | Novel herbicides |
| GB0900641D0 (en) | 2009-01-15 | 2009-02-25 | Syngenta Ltd | Novel herbicides |
| GB0900864D0 (en) | 2009-01-19 | 2009-03-04 | Syngenta Ltd | Novel Herbicides |
| GB0901086D0 (en) | 2009-01-22 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901835D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901834D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| KR101703633B1 (ko) | 2009-03-11 | 2017-02-07 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 할로겐알킬메틸렌옥시페닐-치환된 케토에놀 |
| JP5771189B2 (ja) * | 2009-05-06 | 2015-08-26 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | シクロペンタンジオン化合物、ならびにこの殺虫剤、殺ダニ剤および／または抗真菌剤としての使用 |
| BRPI0924738A2 (pt) * | 2009-05-16 | 2015-08-04 | Syngenta Ltd | Herbicidas |
| ES2540232T3 (es) | 2009-07-08 | 2015-07-09 | Dermira (Canada), Inc. | Análogos de TOFA útiles en el tratamiento de trastornos o afecciones dermatológicas |
| GB0912385D0 (en) | 2009-07-16 | 2009-08-26 | Syngenta Ltd | Novel herbicides |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| CA2816415A1 (en) | 2010-11-02 | 2012-05-10 | Bayer Intellectual Property Gmbh | Phenyl-substituted bicyclooctane-1,3-dione-derivatives |
| DK2806741T3 (da) | 2012-01-26 | 2020-05-18 | Bayer Ip Gmbh | Phenylsubstituerede ketoenoler til bekæmpelse af fiskeparasitter |
| ES2678086T3 (es) | 2013-05-30 | 2018-08-08 | Syngenta Limited | Compuestos de diona cíclicos (alquil-fenil)-sustituidos activos como herbicidas y derivados de los mismos |
| GB201310047D0 (en) | 2013-06-05 | 2013-07-17 | Syngenta Ltd | Compounds |
| US10118890B2 (en) | 2014-10-10 | 2018-11-06 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| GB201621626D0 (en) * | 2016-12-19 | 2017-02-01 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
| AU2024231139A1 (en) * | 2023-03-07 | 2025-07-17 | Bayer Cropscience Lp | Herbicidal compositions comprising fluazifop and triclopyr |
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| PT67818A (en) | 1977-03-28 | 1978-04-01 | Union Carbide Corp | Process for the synthesis of biocidal 2-aryl-1,3-cycloalkanedionas and their enol esters |
| US4659372A (en) | 1977-03-28 | 1987-04-21 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclohexanedione enol ester compounds |
| US4256659A (en) | 1977-03-28 | 1981-03-17 | Union Carbide Corporation | Method of preparing 2-aryl-1,3-cyclohexanedione compounds |
| US4175135A (en) | 1978-07-18 | 1979-11-20 | Union Carbide Corporation | Method of controlling acarina ectoparasites on warmblooded animals by orally administering to the animal an ectoparasitically effective amount of a 2-aryl-1,3-cyclohexanedione compound, and alkali metal salts, ammonium salts and enol esters thereof |
| US4283348A (en) | 1978-09-22 | 1981-08-11 | Union Carbide Corporation | Method of preparing 2-aryl-3-cyclopentanedione compounds |
| US4436666A (en) * | 1978-09-22 | 1984-03-13 | Union Carbide Corporation | Biocidal enol derivatives of 2-aryl-1,3-cycloalkanedione compounds |
| US4526723A (en) | 1978-09-27 | 1985-07-02 | Union Carbide Corporation | Biocidal enol esters of non-ortho substituted 2-aryl-1-3-cycloalkanedione compounds |
| US4371711A (en) | 1979-05-30 | 1983-02-01 | Sumitomo Chemical Company, Limited | Process for producing 4-hydroxycyclopentenones |
| US4338122A (en) | 1979-09-26 | 1982-07-06 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclopentanedione compounds and alkali metal and ammonium salts thereof |
| US4409153A (en) | 1980-03-28 | 1983-10-11 | Union Carbide Corporation | O-(2-Aryl-3-oxo-1-cyclohexenyl) phosphates |
| US4551547A (en) | 1980-11-10 | 1985-11-05 | Union Carbide Corporation | Biocidal 2-aryl-1, 3-cyclopentanedione enol ester compounds |
| US4670041A (en) * | 1981-12-16 | 1987-06-02 | E. I. Du Pont De Nemours And Company | Oxabicycloalkane herbicides |
| US4489012A (en) | 1982-02-23 | 1984-12-18 | Union Carbide Corporation | Enol-phosphorous esters of 2-aryl-1,3-cycloalkanediones compounds |
| US5840661A (en) | 1994-07-07 | 1998-11-24 | Bayer Aktiengesellschaft | 2-aryl cyclopentane-1,3-dione derivatives |
| WO1996003366A1 (de) | 1994-07-21 | 1996-02-08 | Bayer Aktiengesellschaft | 2-(2,4,6-trimethylphenyl)-cyclopentan-1,3-dion-derivate |
| EP0809629B1 (de) | 1995-02-13 | 2004-06-30 | Bayer CropScience AG | 2-phenylsubstituierte heterocyclische 1,3-ketoenole als herbizide und pestizide |
| US6316486B1 (en) | 1995-05-09 | 2001-11-13 | Bayer Aktiengesellschaft | Alkyl dihalogenated phenyl-substituted ketoenols useful as pesticides and herbicides |
| US6515184B1 (en) | 1995-10-13 | 2003-02-04 | Bayer Aktiengesellschaft | Cyclopentane-1,3-dione derivatives, herbicidal and pesticidal compositions containing them, methods of using them to combat pests and weeds and process for the preparation thereof |
| DE19538218A1 (de) | 1995-10-13 | 1997-04-17 | Bayer Ag | Cyclopentan-1,3-dion-Derivate |
| US5723632A (en) * | 1996-08-08 | 1998-03-03 | Mgi Pharma, Inc. | Total synthesis of antitumor acylfulvenes |
| DE19708607A1 (de) | 1997-03-03 | 1998-09-10 | Bayer Ag | 2-Arylcyclopentan-1,3-dione |
| JP2001521250A (ja) | 1997-10-27 | 2001-11-06 | マサチューセッツ・インスティチュート・オブ・テクノロジー | 情報の検索および検索システム |
| DE19808261A1 (de) * | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| DE69908568T2 (de) | 1998-03-13 | 2004-05-06 | Syngenta Participations Ag | Herbizid aktive 3-hydroxy-4-aryl-5-oxopyrazolinderivate |
| DE19813354A1 (de) | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| ES2244214T3 (es) | 1998-09-15 | 2005-12-01 | Syngenta Participations Ag | Piridincetonas utiles como herbicidas. |
| AU2623399A (en) | 1999-02-11 | 2000-08-29 | Novartis Ag | 3-hydroxy-4-aryl-5-pyrazoline derivatives as herbicides |
| DE19935963A1 (de) | 1999-07-30 | 2001-02-01 | Bayer Ag | Biphenylsubstituierte cyclische Ketoenole |
| CN1377358A (zh) | 1999-09-07 | 2002-10-30 | 辛根塔参与股份公司 | 新除草剂 |
| HU229958B1 (hu) | 1999-09-07 | 2015-03-30 | Syngenta Participations Ag | Herbicid vegyületek, ezeket tartalmazó készítmények, eljárás a vegyületek előállítására, valamint eljárás gyomnövények irtására |
| DE10016544A1 (de) | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
| DE10139465A1 (de) | 2001-08-10 | 2003-02-20 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten, cayclischen Ketoenolen und Safenern |
| GB0213638D0 (en) * | 2002-06-13 | 2002-07-24 | Syngenta Ltd | Composition |
| DE10249055A1 (de) | 2002-10-22 | 2004-05-06 | Bayer Cropscience Ag | 2-Phenyl-2-substituierte-1,3-diketone |
| GT200300290A (es) * | 2002-12-30 | 2004-10-13 | Herbicidas novedosos | |
| DE10311300A1 (de) | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
| DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
| DE102004014620A1 (de) | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
| AR049448A1 (es) | 2004-06-22 | 2006-08-02 | Syngenta Participations Ag | Biciclooctenos sustituidos y usos como herbicidas |
| DE102004041529A1 (de) | 2004-08-27 | 2006-03-02 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Ketoenolen |
| DE102004044827A1 (de) | 2004-09-16 | 2006-03-23 | Bayer Cropscience Ag | Jod-phenylsubstituierte cyclische Ketoenole |
| DE102005059471A1 (de) | 2005-12-13 | 2007-07-12 | Bayer Cropscience Ag | Herbizide Zusammensetzungen mit verbesserter Wirkung |
| DE102006000971A1 (de) | 2006-01-07 | 2007-07-12 | Bayer Cropscience Ag | 2,4,6-Trialkylphenylsubstituierte Cyclopentan-1,3-dione |
| DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
| US20100029814A1 (en) | 2006-04-07 | 2010-02-04 | Toshio Inbe | Surface conditioning composition, method for producing the same, and surface conditioning method |
| DE102006018828A1 (de) | 2006-04-22 | 2007-10-25 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
| DE102006025874A1 (de) | 2006-06-02 | 2007-12-06 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
| MY152503A (en) | 2006-12-14 | 2014-10-15 | Syngenta Participations Ag | 4-phenyl-pyrane-3, 5-diones, 4-phenyl-thiopyrane-3, 5-diones and cyclohexanetriones as novel herbicides |
| GB0704652D0 (en) | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
| GB0704653D0 (en) | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
| GB0710223D0 (en) | 2007-05-29 | 2007-07-11 | Syngenta Ltd | Novel Herbicides |
| GB0715454D0 (en) | 2007-08-08 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| GB0715576D0 (en) | 2007-08-09 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| GB0717082D0 (en) | 2007-09-03 | 2007-10-10 | Syngenta Ltd | Novel herbicides |
| GB0812310D0 (en) | 2008-07-03 | 2008-08-13 | Syngenta Ltd | Novel herbicides |
| GB0822834D0 (en) | 2008-12-15 | 2009-01-21 | Syngenta Ltd | Novel herbicides |
| GB0900864D0 (en) | 2009-01-19 | 2009-03-04 | Syngenta Ltd | Novel Herbicides |
| BRPI0924738A2 (pt) | 2009-05-16 | 2015-08-04 | Syngenta Ltd | Herbicidas |
| US8080796B1 (en) | 2010-06-30 | 2011-12-20 | Ut-Battelle, Llc | Standoff spectroscopy using a conditioned target |
| KR20120004209A (ko) | 2010-07-06 | 2012-01-12 | 삼성에스디아이 주식회사 | 리튬 이차 전지용 음극 활물질 및 이를 포함하는 리튬 이차 전지 |
-
2007
- 2007-08-09 GB GBGB0715576.5A patent/GB0715576D0/en not_active Ceased
-
2008
- 2008-04-07 UA UAA201002501A patent/UA96207C2/ru unknown
- 2008-06-27 TW TW097124068A patent/TW200918539A/zh unknown
- 2008-08-07 CN CN2008801025899A patent/CN101903393B/zh active Active
- 2008-08-07 BR BRPI0814926A patent/BRPI0814926B1/pt active IP Right Grant
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