ZA200507570B - 6-alkyl or alkenyl-4-aminopicolinates and their use as herbicides - Google Patents
6-alkyl or alkenyl-4-aminopicolinates and their use as herbicides Download PDFInfo
- Publication number
- ZA200507570B ZA200507570B ZA200507570A ZA200507570A ZA200507570B ZA 200507570 B ZA200507570 B ZA 200507570B ZA 200507570 A ZA200507570 A ZA 200507570A ZA 200507570 A ZA200507570 A ZA 200507570A ZA 200507570 B ZA200507570 B ZA 200507570B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compounds
- amino
- alkenyl
- formula
- Prior art date
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- 239000004009 herbicide Substances 0.000 title description 34
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 29
- 230000002363 herbicidal effect Effects 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000002671 adjuvant Substances 0.000 claims description 8
- 229910052792 caesium Inorganic materials 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 125000005499 phosphonyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- -1 acyleyanide Chemical class 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 19
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 229940081066 picolinic acid Drugs 0.000 description 5
- 230000008635 plant growth Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005561 Glufosinate Substances 0.000 description 3
- 239000005562 Glyphosate Substances 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 229940097068 glyphosate Drugs 0.000 description 3
- XDDAORKBJWWYJS-UHFFFAOYSA-M glyphosate(1-) Chemical compound OP(O)(=O)CNCC([O-])=O XDDAORKBJWWYJS-UHFFFAOYSA-M 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- KIKNEFFJHGIUKZ-UHFFFAOYSA-N methyl 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(F)C(N)=C1Cl KIKNEFFJHGIUKZ-UHFFFAOYSA-N 0.000 description 3
- BIZYCTQHWLCGDB-UHFFFAOYSA-N methyl 4-amino-3-chloro-6-ethenyl-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=NC(C=C)=C(F)C(N)=C1Cl BIZYCTQHWLCGDB-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical class NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 3
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- BFBKUYFMLNOLOQ-UHFFFAOYSA-N 2-butoxyethanamine Chemical compound CCCCOCCN BFBKUYFMLNOLOQ-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- PJHRMQPEENZCPK-UHFFFAOYSA-N 2-methylsulfanylpropan-1-amine Chemical compound CSC(C)CN PJHRMQPEENZCPK-UHFFFAOYSA-N 0.000 description 2
- LMRAMIJXLSBHBC-UHFFFAOYSA-N 4-amino-3-chloro-6-ethyl-5-fluoropyridine-2-carboxylic acid Chemical compound CCC1=NC(C(O)=O)=C(Cl)C(N)=C1F LMRAMIJXLSBHBC-UHFFFAOYSA-N 0.000 description 2
- JRZBTJVSAANBEV-UHFFFAOYSA-N 4-aminopyridine-2-carboxylic acid Chemical class NC1=CC=NC(C(O)=O)=C1 JRZBTJVSAANBEV-UHFFFAOYSA-N 0.000 description 2
- 229930192334 Auxin Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000722731 Carex Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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- 239000005977 Ethylene Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 239000005595 Picloram Substances 0.000 description 2
- 239000002202 Polyethylene glycol Chemical class 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 239000002363 auxin Substances 0.000 description 2
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical class OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- HBGGBCVEFUPUNY-UHFFFAOYSA-N cyclododecanamine Chemical compound NC1CCCCCCCCCCC1 HBGGBCVEFUPUNY-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
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- 150000002431 hydrogen Chemical class 0.000 description 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 2
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- 229960004592 isopropanol Drugs 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- CBZITQGHTYGAJQ-UHFFFAOYSA-N methyl 4-amino-3-chloro-5-fluoro-6-methylpyridine-2-carboxylate Chemical compound COC(=O)C1=NC(C)=C(F)C(N)=C1Cl CBZITQGHTYGAJQ-UHFFFAOYSA-N 0.000 description 2
- JUNQPYUWZOALSZ-UHFFFAOYSA-N methyl 4-amino-3-chloro-6-ethyl-5-fluoropyridine-2-carboxylate Chemical compound CCC1=NC(C(=O)OC)=C(Cl)C(N)=C1F JUNQPYUWZOALSZ-UHFFFAOYSA-N 0.000 description 2
- UYLRKRLDQUXYKB-UHFFFAOYSA-N nickel;triphenylphosphane Chemical compound [Ni].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UYLRKRLDQUXYKB-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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- 229910052763 palladium Inorganic materials 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 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
- 150000007970 thio esters Chemical class 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
- 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
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-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
- 125000002889 tridecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 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
- 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
- 239000003039 volatile agent Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catching Or Destruction (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45989203P | 2003-04-02 | 2003-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200507570B true ZA200507570B (en) | 2006-11-29 |
Family
ID=33159704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200507570A ZA200507570B (en) | 2003-04-02 | 2004-04-02 | 6-alkyl or alkenyl-4-aminopicolinates and their use as herbicides |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7432227B2 (da) |
| EP (1) | EP1608624B1 (da) |
| JP (1) | JP4624990B2 (da) |
| KR (1) | KR101086146B1 (da) |
| CN (1) | CN100519532C (da) |
| AR (1) | AR043829A1 (da) |
| AT (1) | ATE502925T1 (da) |
| AU (1) | AU2004228666B2 (da) |
| BR (1) | BRPI0408935B1 (da) |
| CA (1) | CA2517486C (da) |
| CR (1) | CR7979A (da) |
| DE (1) | DE602004031930D1 (da) |
| DK (1) | DK1608624T3 (da) |
| ES (1) | ES2359917T3 (da) |
| IL (1) | IL171093A (da) |
| MX (1) | MXPA05010615A (da) |
| NO (1) | NO330763B1 (da) |
| NZ (1) | NZ542142A (da) |
| PL (1) | PL1608624T3 (da) |
| PT (1) | PT1608624E (da) |
| RU (1) | RU2332404C2 (da) |
| TW (1) | TWI370816B (da) |
| UA (1) | UA82358C2 (da) |
| WO (1) | WO2004089906A2 (da) |
| ZA (1) | ZA200507570B (da) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005055716A2 (en) * | 2003-12-04 | 2005-06-23 | Syngenta Participations Ag | Herbicidal composition |
| TWI355894B (en) * | 2003-12-19 | 2012-01-11 | Du Pont | Herbicidal pyrimidines |
| WO2006062979A1 (en) * | 2004-12-06 | 2006-06-15 | E.I. Dupont De Nemours And Company | Herbicidal 6-cyclopropyl-substitute 4-aminopicolinic acid derivatives |
| US20090247404A1 (en) * | 2006-02-02 | 2009-10-01 | Bone James R | Method for improving harvestability of crops |
| US7786044B2 (en) | 2007-10-02 | 2010-08-31 | Dow Agrosciences Llc | 2-substituted-6-amino-5-alkyl, alkenyl or alkynyl-4-pyrimidinecarboxylic acids and 6-substituted-4-amino-3- alkyl, alkenyl or alkynyl picolinic acids and their use as herbicides |
| UA106363C2 (ru) * | 2008-12-26 | 2014-08-26 | ДАУ АГРОСАЙЕНСИЗ, ЭлЭлСи | Стабильные инсектицидные композиции на основе сульфоксимина |
| MX2011009024A (es) | 2009-02-27 | 2011-09-29 | Dow Agrosciences Llc | N-alcoxiamidas de 6-(fenil substituido)-4- aminopicolinatos y 2-(fenil substituido)-6-amino-4-pirimidina carboxilatos y su uso como herbicidas selectivos para las cosechas. |
| GB0910766D0 (en) | 2009-06-22 | 2009-08-05 | Syngenta Ltd | Chemical compounds |
| GB0917934D0 (en) | 2009-10-13 | 2009-11-25 | Syngenta Ltd | Herbicidal compounds |
| CN101798282A (zh) * | 2010-03-30 | 2010-08-11 | 中国科学院上海有机化学研究所 | 多取代的含氟吡啶 |
| GB201008290D0 (en) * | 2010-05-18 | 2010-06-30 | Syngenta Ltd | Chemical compounds |
| BR112013009703A2 (pt) | 2010-10-22 | 2018-05-22 | Bayer Ip Gmbh | ácidos picolínicos substituídos, seus sais e derivados de ácidos, bem como seu uso como herbicidas. |
| BR112013014931A2 (pt) | 2010-12-16 | 2016-07-19 | Bayer Ip Gmbh | 6 - (2-aminofenil) - picolinatos e sua utilização como herbicidas |
| TWI547482B (zh) * | 2011-01-25 | 2016-09-01 | 陶氏農業科學公司 | 增加可回收之3-氯-4,5,6-三氟-2-氰吡啶之量的改良方法 |
| TWI592401B (zh) * | 2011-01-25 | 2017-07-21 | 陶氏農業科學公司 | 用於製備４－胺基－３－氯－５－氟－６－（經取代的）吡啶甲酸酯的方法（一） |
| TWI596088B (zh) * | 2011-01-25 | 2017-08-21 | 陶氏農業科學公司 | ４－胺基－６－（經取代的苯基）吡啶甲酸酯及６－胺基－２－（經取代的苯基）－４－嘧啶羧酸酯之芳烷酯以及其等作為除草劑之用途 |
| TWI529163B (zh) | 2011-01-25 | 2016-04-11 | 陶氏農業科學公司 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法 |
| TWI537252B (zh) | 2011-01-25 | 2016-06-11 | 陶氏農業科學公司 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法（一） |
| ES2795438T3 (es) | 2011-06-30 | 2020-11-23 | Dow Agrosciences Llc | 3-alcoxi, tioalquilo y amino-4-amino-6-(sustituido)picolinatos y su uso como herbicidas |
| AR092355A1 (es) | 2012-07-24 | 2015-04-15 | Dow Agrosciences Llc | Fluoruros de fluoropicolinoilo y procesos para su preparacion |
| AR091856A1 (es) * | 2012-07-24 | 2015-03-04 | Dow Agrosciences Llc | Proceso para la preparacion de 4-amino-5-fluor-3-halo-6-(substituido) picolinatos |
| US9320274B2 (en) | 2012-09-04 | 2016-04-26 | Dow Agrosciences Llc | Synergistic weed control from applications of aminocyclopyrachlor and clopyralid |
| CA2884518A1 (en) | 2012-09-28 | 2014-04-03 | Dow Agrosciences Llc | Synergistic weed control from applications of aminocyclopyrachlor and triclopyr |
| CN102845429B (zh) * | 2012-09-28 | 2014-08-13 | 山东潍坊润丰化工股份有限公司 | 一种毒莠定胆碱水剂和原药的制备方法 |
| CN110583666A (zh) | 2012-09-28 | 2019-12-20 | 美国陶氏益农公司 | 来自施用环丙嘧啶酸和氯氟吡氧乙酸的协同杂草控制 |
| NZ706387A (en) | 2012-09-28 | 2018-07-27 | Dow Agrosciences Llc | Synergistic weed control from applications of aminocyclopyrachlor and aminopyralid |
| US9149037B2 (en) | 2012-12-12 | 2015-10-06 | Dow Agrosciences Llc | Synergistic weed control from applications of aminocyclopyrachlor and 2,4 dichlorophenoxyacetic acid (2,4-D) |
| WO2014093346A1 (en) | 2012-12-12 | 2014-06-19 | Dow Agrosciences Llc | Synergistic weed control from applications of penoxsulam and mefenacet |
| US9426991B2 (en) | 2012-12-12 | 2016-08-30 | Dow Agrosciences Llc | Synergistic weed control from applications of aminocyclopyrachlor and picloram |
| BR102013032022A2 (pt) | 2012-12-13 | 2014-10-21 | Dow Agrosciences Llc | Processo para a preparação de 4-amino-5-fluoro-3-cloro-6-(substituído)picolinatos |
| NZ708681A (en) * | 2012-12-13 | 2016-09-30 | Dow Agrosciences Llc | Processes for the preparation of 4-amino-3-halo-6- (substituted)picolinates and 4-amino-5-fluoro-3-halo-6- (substituted)picolinates |
| EP2931043B1 (en) | 2012-12-13 | 2017-08-02 | Dow AgroSciences LLC | Process for the preparation of 4-amino-5-fluoro-3-chloro-6-(substituted)picolinates |
| KR20150097595A (ko) | 2012-12-14 | 2015-08-26 | 다우 아그로사이언시즈 엘엘씨 | 아미노피랄리드 및 클로피랄리드의 적용에 의한 상승작용적 잡초 방제 |
| US10412964B2 (en) | 2012-12-14 | 2019-09-17 | Dow Agrosciences Llc | Synergistic weed control from applications of aminopyralid and clopyralid |
| WO2014100465A2 (en) | 2012-12-21 | 2014-06-26 | Dow Agrosciences Llc | Temperature stable cloquintocet-mexyl aqueous compositions |
| EP2934112B1 (en) | 2012-12-21 | 2019-05-08 | Dow Agrosciences LLC | Herbicide containing aminopyralid, triclopyr and organosilicone surfactant |
| MY173055A (en) | 2013-02-25 | 2019-12-23 | Dow Agrosciences Llc | Synergistic weed control from applications of penoxsulam and acetochlor |
| WO2014130661A1 (en) | 2013-02-25 | 2014-08-28 | Dow Agrosciences Llc | Methods of weed control in pineapple |
| PT2967037T (pt) | 2013-03-15 | 2019-03-21 | Dow Agrosciences Llc | Controlo sinérgico de infestantes através de aplicações de penoxsulame e benzobiciclão ou clomazona e benzobiciclão |
| EP2967051B1 (en) | 2013-03-15 | 2018-08-08 | Dow AgroSciences LLC | Synergistic weed control from applications of penoxsulam and pethoxamid |
| WO2015048269A1 (en) | 2013-09-25 | 2015-04-02 | Dow Agrosciences Llc | Methods of weed control in chicory |
| WO2015099993A1 (en) * | 2013-12-12 | 2015-07-02 | Dow Agrosciences Llc | 4-amino-6-(halo-substituted-alkyl)-picolinates and their use as herbicides |
| TWI694770B (zh) | 2014-09-15 | 2020-06-01 | 美商陶氏農業科學公司 | 包含吡啶羧酸除草劑之安全的除草組成物（二） |
| TWI685302B (zh) | 2014-09-15 | 2020-02-21 | 美商陶氏農業科學公司 | 包含吡啶羧酸除草劑之安全的除草組成物 |
| TWI689252B (zh) | 2014-09-15 | 2020-04-01 | 美商陶氏農業科學公司 | 源自於施用吡啶羧酸除草劑與乙醯乳酸合成酶（ａｌｓ）抑制劑的協同性雜草控制 |
| WO2017027442A1 (en) * | 2015-08-10 | 2017-02-16 | Dow Agrosciences Llc | Safened herbicidal compositions comprising pyridine carboxylic acids |
| WO2017027441A1 (en) * | 2015-08-10 | 2017-02-16 | Dow Agrosciences Llc | Safened herbicidal compositions comprising pyridine carboxylic acids |
| BR102016019512B8 (pt) | 2015-08-26 | 2022-10-11 | Dow Agrosciences Llc | Composição compreendendo complexo protetor compreendendo cloquintocet e polímeros ou oligômeros contendo amina, seu método de preparação, e método para controle da vegetação indesejável |
| MX2018008842A (es) | 2016-01-19 | 2018-09-17 | Dow Agrosciences Llc | Sales de cloquintocet para proteger composiciones de piroxsulam. |
| AU2017287716B2 (en) * | 2016-06-27 | 2019-08-08 | Korea Research Institute Of Chemical Technology | Pyridine-based compound including isoxazoline ring, and use thereof as herbicide |
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| CN106550946A (zh) * | 2016-11-16 | 2017-04-05 | 江苏省农业科学院 | 一种含氨氯吡啶酸和乙氧氟草醚的农药组合物及其应用 |
| TW202010408A (zh) | 2018-04-04 | 2020-03-16 | 美商陶氏農業科學公司 | 施用吡啶甲酸除草劑及乙醯輔酶ａ羧化酶（ａｃｃ酶）抑制劑而改善雜草控制 |
| TW202002784A (zh) | 2018-04-04 | 2020-01-16 | 美商陶氏農業科學公司 | 施用吡啶甲酸除草劑及４—羥基苯基—丙酮酸酯雙加氧酶（ｈｐｐｄ）抑制劑的雜草控制 |
| EP3793360A4 (en) | 2018-05-16 | 2022-02-16 | University of Florida Research Foundation | Methods and compositions for substituted 2,5-diketopiperazine analogs |
| CA3118680A1 (en) | 2018-11-06 | 2020-05-14 | Corteva Agriscience Llc | Compositions comprising pyridine carboxylate herbicides and azole carboxylate safeners |
| UA128373C2 (uk) | 2018-11-06 | 2024-06-26 | Кортева Аґрисайєнс Елелсі | Композиції з антидотом, які містять гербіциди на основі піридинкарбоксилату та ізоксадифен |
| CA3119026A1 (en) | 2018-11-06 | 2020-05-14 | Corteva Agriscience Llc | Safened compositions comprising pyridine carboxylate herbicides and cloquintocet |
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| EP3876729B1 (en) | 2018-11-07 | 2025-01-01 | Corteva Agriscience LLC | Compositions comprising a pyridine carboxylate herbicide and protoporphyrinogen oxidase (protox) inhibitor herbicides |
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| US3285925A (en) | 1962-03-06 | 1966-11-15 | Dow Chemical Co | Amino-trichloropicolinic acid compounds |
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-
2004
- 2004-02-04 UA UAA200510324A patent/UA82358C2/uk unknown
- 2004-03-31 TW TW093108894A patent/TWI370816B/zh not_active IP Right Cessation
- 2004-04-01 AR ARP040101109A patent/AR043829A1/es not_active Application Discontinuation
- 2004-04-02 CN CNB2004800078000A patent/CN100519532C/zh not_active Expired - Fee Related
- 2004-04-02 ES ES04749733T patent/ES2359917T3/es not_active Expired - Lifetime
- 2004-04-02 KR KR1020057018682A patent/KR101086146B1/ko not_active Expired - Fee Related
- 2004-04-02 WO PCT/US2004/010358 patent/WO2004089906A2/en active Application Filing
- 2004-04-02 JP JP2006509682A patent/JP4624990B2/ja not_active Expired - Fee Related
- 2004-04-02 ZA ZA200507570A patent/ZA200507570B/en unknown
- 2004-04-02 DK DK04749733.4T patent/DK1608624T3/da active
- 2004-04-02 AT AT04749733T patent/ATE502925T1/de active
- 2004-04-02 DE DE602004031930T patent/DE602004031930D1/de not_active Expired - Lifetime
- 2004-04-02 CA CA2517486A patent/CA2517486C/en not_active Expired - Fee Related
- 2004-04-02 PT PT04749733T patent/PT1608624E/pt unknown
- 2004-04-02 EP EP04749733A patent/EP1608624B1/en not_active Expired - Lifetime
- 2004-04-02 AU AU2004228666A patent/AU2004228666B2/en not_active Ceased
- 2004-04-02 RU RU2005133716/04A patent/RU2332404C2/ru not_active IP Right Cessation
- 2004-04-02 NZ NZ542142A patent/NZ542142A/en not_active IP Right Cessation
- 2004-04-02 MX MXPA05010615A patent/MXPA05010615A/es active IP Right Grant
- 2004-04-02 PL PL04749733T patent/PL1608624T3/pl unknown
- 2004-04-02 US US10/816,611 patent/US7432227B2/en not_active Expired - Lifetime
- 2004-04-02 BR BRPI0408935-9A patent/BRPI0408935B1/pt not_active IP Right Cessation
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2005
- 2005-09-07 CR CR7979A patent/CR7979A/es unknown
- 2005-09-21 NO NO20054378A patent/NO330763B1/no not_active IP Right Cessation
- 2005-09-26 IL IL171093A patent/IL171093A/en active IP Right Grant
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