ZA200509176B - N-Alkynyl-2-(Substituted aryloxy) alkylthioamide derivatives as fungicides - Google Patents
N-Alkynyl-2-(Substituted aryloxy) alkylthioamide derivatives as fungicides Download PDFInfo
- Publication number
- ZA200509176B ZA200509176B ZA200509176A ZA200509176A ZA200509176B ZA 200509176 B ZA200509176 B ZA 200509176B ZA 200509176 A ZA200509176 A ZA 200509176A ZA 200509176 A ZA200509176 A ZA 200509176A ZA 200509176 B ZA200509176 B ZA 200509176B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- halo
- alkoxy
- methyl
- optionally substituted
- Prior art date
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- 125000004104 aryloxy group Chemical group 0.000 title claims description 9
- 239000000417 fungicide Substances 0.000 title description 3
- 125000005843 halogen group Chemical group 0.000 claims description 263
- 125000000217 alkyl group Chemical group 0.000 claims description 259
- -1 nitro, amino Chemical group 0.000 claims description 253
- 150000001875 compounds Chemical class 0.000 claims description 228
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 212
- 125000003545 alkoxy group Chemical group 0.000 claims description 131
- 229910052739 hydrogen Inorganic materials 0.000 claims description 88
- 125000004414 alkyl thio group Chemical group 0.000 claims description 82
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 62
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 49
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 46
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000000304 alkynyl group Chemical group 0.000 claims description 39
- 125000001246 bromo group Chemical group Br* 0.000 claims description 39
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims description 37
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 27
- 125000003282 alkyl amino group Chemical group 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 18
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 12
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 12
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 10
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000000815 N-oxide group Chemical group 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 claims description 4
- 125000004011 3 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000001845 4 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 239000001963 growth medium Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 description 114
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 125000006416 CBr Chemical group BrC* 0.000 description 9
- 125000003107 substituted aryl group Chemical group 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000006414 CCl Chemical group ClC* 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical class O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000005554 pyridyloxy group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- 125000005955 1H-indazolyl group Chemical group 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000080590 Niso Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/29—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
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- 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)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0312863.4A GB0312863D0 (en) | 2003-06-04 | 2003-06-04 | Fungicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200509176B true ZA200509176B (en) | 2007-03-28 |
Family
ID=9959327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200509176A ZA200509176B (en) | 2003-06-04 | 2005-11-14 | N-Alkynyl-2-(Substituted aryloxy) alkylthioamide derivatives as fungicides |
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| Country | Link |
|---|---|
| US (1) | US8067592B2 (ru) |
| EP (1) | EP1638928B1 (ru) |
| JP (1) | JP4723482B2 (ru) |
| KR (1) | KR20060017631A (ru) |
| CN (1) | CN100540534C (ru) |
| AR (1) | AR045684A1 (ru) |
| AT (1) | ATE482932T1 (ru) |
| AU (1) | AU2004245282B2 (ru) |
| BR (1) | BRPI0410995A (ru) |
| CA (1) | CA2527313A1 (ru) |
| CL (1) | CL2004001407A1 (ru) |
| CO (1) | CO5640048A2 (ru) |
| CR (1) | CR8107A (ru) |
| DE (1) | DE602004029363D1 (ru) |
| DK (1) | DK1638928T3 (ru) |
| EC (1) | ECSP056195A (ru) |
| ES (1) | ES2353124T3 (ru) |
| GB (1) | GB0312863D0 (ru) |
| GT (1) | GT200400107A (ru) |
| IL (1) | IL172024A (ru) |
| MX (1) | MXPA05013039A (ru) |
| PL (1) | PL1638928T3 (ru) |
| PT (1) | PT1638928E (ru) |
| RU (1) | RU2352559C2 (ru) |
| SI (1) | SI1638928T1 (ru) |
| TW (1) | TWI326584B (ru) |
| WO (1) | WO2004108663A1 (ru) |
| ZA (1) | ZA200509176B (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0227554D0 (en) * | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| GB0227551D0 (en) | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| GB0227556D0 (en) | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| GB0227555D0 (en) | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| GB0426373D0 (en) * | 2004-12-01 | 2005-01-05 | Syngenta Ltd | Fungicides |
| GB0426372D0 (en) * | 2004-12-01 | 2005-01-05 | Syngenta Ltd | Fungicides |
| GB0617574D0 (en) * | 2006-09-06 | 2006-10-18 | Syngenta Participations Ag | Fungicides |
| GB0717258D0 (en) * | 2007-09-05 | 2007-10-17 | Syngenta Participations Ag | Novel fungicides |
| GB0717260D0 (en) * | 2007-09-05 | 2007-10-17 | Syngenta Participations Ag | Novel fungicides |
| GB0717256D0 (en) | 2007-09-05 | 2007-10-17 | Syngenta Participations Ag | Novel fungicides |
| GB0800407D0 (en) * | 2008-01-10 | 2008-02-20 | Syngenta Participations Ag | Fungicides |
| WO2010015680A1 (en) * | 2008-08-07 | 2010-02-11 | Bayer Cropscience Sa | Fungicide oxyalkylamide derivatives |
| EP2571851A1 (en) * | 2010-05-21 | 2013-03-27 | Syngenta Participations AG | Novel amides as fungicides |
| TWI504350B (zh) | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
| TWI568721B (zh) | 2012-02-01 | 2017-02-01 | 杜邦股份有限公司 | 殺真菌之吡唑混合物 |
| WO2013126283A1 (en) | 2012-02-20 | 2013-08-29 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| JP2013216626A (ja) * | 2012-04-10 | 2013-10-24 | Nippon Soda Co Ltd | アリールオキシ酢酸アミド化合物を含有する殺ダニ剤または殺虫剤 |
| PL2864293T3 (pl) | 2012-06-22 | 2016-12-30 | Grzybobójcze 4-metyloanilinopirazole | |
| CN103125492B (zh) * | 2013-01-21 | 2014-03-26 | 西华大学 | 新型硫代乙酰胺类化合物及其作为除草剂的用途 |
| WO2014130409A2 (en) | 2013-02-21 | 2014-08-28 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazole mixtures |
| PL2986601T3 (pl) | 2013-04-15 | 2017-10-31 | Fmc Corp | Karboksyamidy o działaniu grzybobójczym |
| MX2015014407A (es) | 2013-04-15 | 2015-12-07 | Du Pont | Amidas fungicidas. |
| WO2015123193A1 (en) | 2014-02-12 | 2015-08-20 | E. I. Du Pont De Nemours And Company | Fungicidal benzodipyrazoles |
| WO2015157005A1 (en) | 2014-04-10 | 2015-10-15 | E I Du Pont De Nemours And Company | Substituted tolyl fungicide mixtures |
| EP3140289A1 (en) | 2014-05-06 | 2017-03-15 | E. I. du Pont de Nemours and Company | Fungicidal pyrazoles |
| JP2018510155A (ja) | 2015-03-19 | 2018-04-12 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 殺菌・殺カビ性ピラゾール |
| CN105753802B (zh) * | 2016-04-27 | 2018-06-05 | 广东环境保护工程职业学院 | 3-异丙基-6-溴苯并异噁唑及其制备方法 |
| PL3558984T3 (pl) | 2016-12-20 | 2024-01-15 | Fmc Corporation | Oksadiazole grzybobójcze |
| TW202334101A (zh) | 2017-04-06 | 2023-09-01 | 美商富曼西公司 | 殺真菌之噁二唑 |
| AR112221A1 (es) | 2017-07-05 | 2019-10-02 | Fmc Corp | Oxadiazoles fungicidas, composición que los comprende y un método para controlar fitoenfermedades que los emplea |
| TWI819078B (zh) | 2018-09-06 | 2023-10-21 | 美商富曼西公司 | 殺真菌之經硝苯胺基取代之吡唑 |
| CN113015433A (zh) | 2018-09-14 | 2021-06-22 | Fmc公司 | 杀真菌卤代甲基酮及水合物 |
| TWI832917B (zh) | 2018-11-06 | 2024-02-21 | 美商富曼西公司 | 經取代之甲苯基殺真菌劑 |
| CA3167647A1 (en) | 2020-01-15 | 2021-07-22 | Fmc Corporation | Fungicidal amides |
| AU2021219788A1 (en) | 2020-02-14 | 2022-09-08 | Fmc Corporation | Substituted 5,6-diphenyl-3(2H)-pyridazinones for use as fungicides |
| CN113861223B (zh) * | 2021-09-07 | 2022-09-16 | 暨南大学 | 一种噻唑并[3,2-a]苯并咪唑类化合物的合成方法及其应用 |
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| CS189773B2 (en) | 1975-06-30 | 1979-04-30 | Stauffer Chemical Co | Acaricide means |
| US4049423A (en) | 1975-06-30 | 1977-09-20 | Stauffer Chemical Company | N-dimethylpropynyl-α-methoxy-α-(3,5-dimethylphenoxy)acetamide herbicide |
| IN146297B (ru) | 1976-07-30 | 1979-04-14 | Stauffer Chemical Co | |
| AR220917A1 (es) | 1977-10-26 | 1980-12-15 | Stauffer Chemical Co | Compuestos de n-sustituido-2-(4 sustituido-3,5-dimetilfenoxi)butiramida utiles como anublicidas y composicion que los contiene |
| US4154849A (en) | 1977-10-26 | 1979-05-15 | Stauffer Chemical Company | N-Cyano-2-(substituted phenoxy) butyramides and their use as mildewicides |
| US4168319A (en) | 1977-10-26 | 1979-09-18 | Stauffer Chemical Company | N-alkynyl-2-(substituted phenoxy) butyramides and their use as mildewicides |
| US4146387A (en) | 1977-11-25 | 1979-03-27 | Stauffer Chemical Company | Synergistic herbicidal compositions |
| DE2846127A1 (de) * | 1978-10-23 | 1980-04-30 | Basf Ag | 1,2,4-triazol-1-yl-verbindungen, ihre hersttellung und verwendung als fungizide |
| DE2948095A1 (de) | 1979-11-29 | 1981-06-19 | Hoechst Ag, 6230 Frankfurt | Phenoxialkan- und phenoxialkencarbonsaeuren und deren derivate, ihre herstellung und verwendung |
| DE3418168A1 (de) | 1984-05-16 | 1985-11-21 | Bayer Ag, 5090 Leverkusen | 6-chlorbenzazolyloxyacetamide |
| US4873346A (en) | 1985-09-20 | 1989-10-10 | The Upjohn Company | Substituted benzothiazoles, benzimidazoles, and benzoxazoles |
| JPS62209056A (ja) * | 1986-03-10 | 1987-09-14 | Mitsui Toatsu Chem Inc | ベンズアミド誘導体、その製造法およびそれらを含有する除草剤および農園芸用殺菌剤 |
| DE3702964A1 (de) | 1987-01-30 | 1988-08-11 | Shell Agrar Gmbh & Co Kg | Aryloxycarbonsaeurederivate, ihre herstellung und verwendung |
| US5166390A (en) * | 1990-01-05 | 1992-11-24 | Rohm And Haas Company | S-substituted carbonyl substituted beta-thioacrylamide biocides and fungicides |
| JP2856840B2 (ja) | 1990-05-15 | 1999-02-10 | 株式会社トクヤマ | チエニルオキシフェノキシカルボン酸誘導体 |
| JPH06186702A (ja) | 1992-12-18 | 1994-07-08 | Konica Corp | ハロゲン化銀カラー反転写真感光材料 |
| US5733935A (en) | 1995-06-29 | 1998-03-31 | Nihon Nohyaku Co., Ltd. | Hydroxylamine derivatives and fungicides containing the same |
| US6130217A (en) | 1995-09-20 | 2000-10-10 | Pfizer Inc | Compounds enhancing antitumor activity of other cytotoxic agents |
| AU3759697A (en) | 1996-10-01 | 1998-04-09 | Rohm And Haas Company | Process for amines |
| AU4725497A (en) | 1996-10-31 | 1998-05-22 | Kumiai Chemical Industry Co., Ltd. | Pyrimidinyloxyalkanoic amide derivatives and fungicides for agricultural and horticultural use |
| JP2003526594A (ja) | 1997-07-14 | 2003-09-09 | アドラー コーポレーション | カッパ・アゴニスト抗掻痒薬学的製剤およびそれにより掻痒を治療する方法 |
| JPH11158131A (ja) * | 1997-08-13 | 1999-06-15 | Kumiai Chem Ind Co Ltd | アリ−ル酢酸アミド誘導体及び農園芸用殺菌剤 |
| JPH11263776A (ja) * | 1997-12-24 | 1999-09-28 | Kumiai Chem Ind Co Ltd | ピリジルオキシ（チオ）アルカン酸アミド誘導体及び農園芸用殺菌剤 |
| WO1999033810A1 (fr) | 1997-12-24 | 1999-07-08 | Kumiai Chemical Industry Co., Ltd. | Derives amides d'acide pyridyloxy(thio)alcanoique et bactericides a usage agricole ou horticole |
| GB0129267D0 (en) | 2001-12-06 | 2002-01-23 | Syngenta Ltd | Fungicides |
| GB0227556D0 (en) | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| GB0227558D0 (en) | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| GB0227557D0 (en) | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| GB0227555D0 (en) | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| GB0227554D0 (en) | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| GB0302308D0 (en) | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin and avermectin monosaccharide derivatives substituted in the 4"- or 4'-position having pesticidal properties |
| GB0312864D0 (en) | 2003-06-04 | 2003-07-09 | Syngenta Ltd | Fungicides |
| GB0426373D0 (en) | 2004-12-01 | 2005-01-05 | Syngenta Ltd | Fungicides |
| GB0426372D0 (en) | 2004-12-01 | 2005-01-05 | Syngenta Ltd | Fungicides |
-
2003
- 2003-06-04 GB GBGB0312863.4A patent/GB0312863D0/en not_active Ceased
-
2004
- 2004-05-12 TW TW093113305A patent/TWI326584B/zh not_active IP Right Cessation
- 2004-05-18 AR ARP040101715A patent/AR045684A1/es unknown
- 2004-05-26 GT GT200400107A patent/GT200400107A/es unknown
- 2004-05-28 MX MXPA05013039A patent/MXPA05013039A/es active IP Right Grant
- 2004-05-28 DK DK04735260.4T patent/DK1638928T3/da active
- 2004-05-28 RU RU2005141530/04A patent/RU2352559C2/ru not_active IP Right Cessation
- 2004-05-28 KR KR1020057023219A patent/KR20060017631A/ko active IP Right Grant
- 2004-05-28 CA CA002527313A patent/CA2527313A1/en not_active Abandoned
- 2004-05-28 US US10/558,116 patent/US8067592B2/en not_active Expired - Fee Related
- 2004-05-28 AT AT04735260T patent/ATE482932T1/de active
- 2004-05-28 EP EP04735260A patent/EP1638928B1/en not_active Expired - Lifetime
- 2004-05-28 AU AU2004245282A patent/AU2004245282B2/en not_active Ceased
- 2004-05-28 SI SI200431573T patent/SI1638928T1/sl unknown
- 2004-05-28 CN CNB2004800182979A patent/CN100540534C/zh not_active Expired - Fee Related
- 2004-05-28 WO PCT/GB2004/002294 patent/WO2004108663A1/en active Application Filing
- 2004-05-28 PT PT04735260T patent/PT1638928E/pt unknown
- 2004-05-28 DE DE602004029363T patent/DE602004029363D1/de not_active Expired - Lifetime
- 2004-05-28 JP JP2006508378A patent/JP4723482B2/ja not_active Expired - Fee Related
- 2004-05-28 BR BRPI0410995-3A patent/BRPI0410995A/pt not_active Application Discontinuation
- 2004-05-28 PL PL04735260T patent/PL1638928T3/pl unknown
- 2004-05-28 ES ES04735260T patent/ES2353124T3/es not_active Expired - Lifetime
- 2004-06-04 CL CL200401407A patent/CL2004001407A1/es unknown
-
2005
- 2005-11-14 ZA ZA200509176A patent/ZA200509176B/en unknown
- 2005-11-17 IL IL172024A patent/IL172024A/en not_active IP Right Cessation
- 2005-11-30 EC EC2005006195A patent/ECSP056195A/es unknown
- 2005-11-30 CR CR8107A patent/CR8107A/es not_active Application Discontinuation
- 2005-12-01 CO CO05122025A patent/CO5640048A2/es not_active Application Discontinuation
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