TW200303170A - 2-Amino-4-bicyclylamino-6H-1,3,5-triazines,processes for their preparation and their use as herbicides and plant growth regulators - Google Patents
2-Amino-4-bicyclylamino-6H-1,3,5-triazines,processes for their preparation and their use as herbicides and plant growth regulators Download PDFInfo
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- TW200303170A TW200303170A TW092103329A TW92103329A TW200303170A TW 200303170 A TW200303170 A TW 200303170A TW 092103329 A TW092103329 A TW 092103329A TW 92103329 A TW92103329 A TW 92103329A TW 200303170 A TW200303170 A TW 200303170A
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- Prior art keywords
- group
- alkyl
- groups
- alkoxy
- heterocyclic
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- 239000004009 herbicide Substances 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 31
- 239000005648 plant growth regulator Substances 0.000 title abstract description 6
- 238000002360 preparation method Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 150000003839 salts Chemical class 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 306
- -1 carbocyclic radical Chemical class 0.000 claims description 231
- 125000003545 alkoxy group Chemical group 0.000 claims description 108
- 241000196324 Embryophyta Species 0.000 claims description 99
- 125000000623 heterocyclic group Chemical group 0.000 claims description 99
- 125000004432 carbon atom Chemical group C* 0.000 claims description 89
- 125000004122 cyclic group Chemical group 0.000 claims description 89
- 229910052736 halogen Inorganic materials 0.000 claims description 86
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 83
- 150000002367 halogens Chemical class 0.000 claims description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
- 150000003254 radicals Chemical class 0.000 claims description 72
- 150000001412 amines Chemical class 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000000460 chlorine Substances 0.000 claims description 63
- 125000001188 haloalkyl group Chemical group 0.000 claims description 55
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 45
- 125000003277 amino group Chemical group 0.000 claims description 43
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 43
- 125000000304 alkynyl group Chemical group 0.000 claims description 39
- 125000006413 ring segment Chemical group 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000003282 alkyl amino group Chemical group 0.000 claims description 32
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000004414 alkyl thio group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 230000002363 herbicidal effect Effects 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 125000004043 oxo group Chemical group O=* 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 17
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 13
- 125000002837 carbocyclic group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000000468 ketone group Chemical group 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 230000012010 growth Effects 0.000 claims description 10
- 125000002015 acyclic group Chemical group 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000004470 heterocyclooxy group Chemical group 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 230000008635 plant growth Effects 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 7
- 230000001276 controlling effect Effects 0.000 claims description 7
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000004149 thio group Chemical group *S* 0.000 claims description 7
- 229930194542 Keto Natural products 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010586 diagram Methods 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 238000007347 radical substitution reaction Methods 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- XMDBJQOQTPRRJM-UHFFFAOYSA-N 1-nitro-n-oxido-n-oxomethanimidamide Chemical compound NC(=N)[N+]([O-])=O XMDBJQOQTPRRJM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 150000001350 alkyl halides Chemical group 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 125000004427 diamine group Chemical group 0.000 claims description 3
- 238000009313 farming Methods 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004354 sulfur functional group Chemical group 0.000 claims description 3
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical group 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 150000007857 hydrazones Chemical class 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 235000007516 Chrysanthemum Nutrition 0.000 claims 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 102100038374 Pinin Human genes 0.000 claims 1
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- 239000002671 adjuvant Substances 0.000 claims 1
- 125000002355 alkine group Chemical group 0.000 claims 1
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- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
- 238000013329 compounding Methods 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- UOKZUTXLHRTLFH-UHFFFAOYSA-N o-phenylhydroxylamine Chemical compound NOC1=CC=CC=C1 UOKZUTXLHRTLFH-UHFFFAOYSA-N 0.000 claims 1
- 125000002347 octyl 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])[H] 0.000 claims 1
- 229920001484 poly(alkylene) Polymers 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 12
- 239000002585 base Substances 0.000 description 50
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- 239000000126 substance Substances 0.000 description 25
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
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- 230000000694 effects Effects 0.000 description 17
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- HZDIJTXDRLNTIS-DAXSKMNVSA-N n-[[(z)-but-2-enoxy]methyl]-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(COC\C=C/C)C(=O)CCl HZDIJTXDRLNTIS-DAXSKMNVSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NMBXMBCZBXUXAM-UHFFFAOYSA-N n-butyl-1-dibutoxyphosphorylcyclohexan-1-amine Chemical compound CCCCOP(=O)(OCCCC)C1(NCCCC)CCCCC1 NMBXMBCZBXUXAM-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
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- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
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- 230000008520 organization Effects 0.000 description 1
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- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
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- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
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- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FHHJDRFHHWUPDG-UHFFFAOYSA-L peroxysulfate(2-) Chemical compound [O-]OS([O-])(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-L 0.000 description 1
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- 150000003009 phosphonic acids Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
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- 229920000570 polyether Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
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- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
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- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
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- 150000003460 sulfonic acids Chemical class 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
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- 230000001131 transforming effect Effects 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
- 125000001425 triazolyl group Chemical group 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
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000052 vinegar Chemical class 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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- 239000011592 zinc chloride Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10207037A DE10207037A1 (de) | 2002-02-20 | 2002-02-20 | 2-Amino-4-bicyclyamino-6H-1,3.5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200303170A true TW200303170A (en) | 2003-09-01 |
Family
ID=27635161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092103329A TW200303170A (en) | 2002-02-20 | 2003-02-18 | 2-Amino-4-bicyclylamino-6H-1,3,5-triazines,processes for their preparation and their use as herbicides and plant growth regulators |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7479471B2 (enExample) |
| EP (1) | EP1478628B1 (enExample) |
| JP (1) | JP4755396B2 (enExample) |
| KR (1) | KR101107877B1 (enExample) |
| CN (1) | CN100491359C (enExample) |
| AR (1) | AR038562A1 (enExample) |
| AT (1) | ATE410416T1 (enExample) |
| AU (2) | AU2003212235A1 (enExample) |
| BR (1) | BR0307877B1 (enExample) |
| CA (1) | CA2476828C (enExample) |
| DE (2) | DE10207037A1 (enExample) |
| ES (1) | ES2312754T3 (enExample) |
| MX (1) | MXPA04008044A (enExample) |
| MY (1) | MY138410A (enExample) |
| NZ (1) | NZ534737A (enExample) |
| RU (1) | RU2004127931A (enExample) |
| TW (1) | TW200303170A (enExample) |
| WO (1) | WO2003070710A1 (enExample) |
| ZA (1) | ZA200405699B (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19921883A1 (de) * | 1999-05-12 | 2000-11-16 | Bayer Ag | Substituierte Thienocycloalk(en)ylamino-1,3,5-triazine |
| OA13024A (en) * | 2003-02-05 | 2006-11-10 | Bayer Cropscience Gmbh | Amino 1, 3, 5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof and their use as herbicides and plant growth regulators. |
| DE102004034571A1 (de) * | 2004-07-17 | 2006-02-23 | Bayer Cropscience Gmbh | Herbizide Mittel |
| EP1790227A1 (de) | 2005-11-25 | 2007-05-30 | Bayer CropScience AG | Wässrige Suspensionskonzentrate aus 2,4-Diamino-s-triazinherbiziden |
| JP5188988B2 (ja) * | 2006-02-10 | 2013-04-24 | トランステック ファーマ，インコーポレイティド | ベンゾアゾール誘導体、組成物、及びオーロラキナーゼ阻害剤としての使用方法 |
| EP1854355A1 (de) * | 2006-03-15 | 2007-11-14 | Bayer CropScience AG | Wässrige Suspensionskonzentrate |
| DE102006016884A1 (de) * | 2006-04-11 | 2007-10-25 | Bayer Cropscience Ag | Substituierte Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| EP1958509A1 (de) * | 2007-02-19 | 2008-08-20 | Bayer CropScience AG | Herbizid-Kombination |
| EP2147600A1 (en) * | 2008-07-21 | 2010-01-27 | Bayer CropScience AG | Method for weed control in lawn |
| RU2013133873A (ru) | 2010-12-21 | 2015-01-27 | БАЙЕР КРОПСАЙЕНС ЭлПи | ШЕРОХОВАТЫЕ МУТАНТЫ Bacillus И СПОСОБЫ ИХ ПРИМЕНЕНИЯ ДЛЯ УСКОРЕНИЯ РОСТА РАСТЕНИЙ, УЛУЧШЕНИЯ ЗДОРОВЬЯ РАСТЕНИЙ И БОРЬБЫ С БОЛЕЗНЯМИ И ВРЕДИТЕЛЯМИ |
| WO2012135166A1 (en) * | 2011-03-28 | 2012-10-04 | Pathway Therapeutics Inc. | (fused ring arylamino and heterocyclylamino) pyrimidynyl and 1,3,5-triazinyl benzimidazoles, pharmaceutical compositions thereof, and their use in treating proliferative diseases |
| BR112013024907A2 (pt) | 2011-03-28 | 2016-12-20 | Mei Pharma Inc | composto, composição farmacêutica, método para o tratamento, prevenção ou atenuação de um ou mais sintomas de um distúrbio, doença ou condição mediada por pi3k em um sujeito, método para modular a atividade enzimática de pi3k |
| EP2755485A1 (en) | 2011-09-12 | 2014-07-23 | Bayer Cropscience LP | Methods of enhancing health and/or promoting growth of a plant and/or of improving fruit ripening |
| RU2509770C2 (ru) * | 2012-06-22 | 2014-03-20 | Общество с ограниченной ответственностью "Молекулярные Технологии" | Новые химические соединения производные 2,4-диамино-1,3,5-триазина для профилактики и лечения заболеваний человека и животных |
| WO2015047124A1 (ru) * | 2013-09-26 | 2015-04-02 | Общество с ограниченной ответственностью "Молекулярные Технологии" | Новые химические соединения производные 2,4-диамино-1,3,5-триазина для профилактики и лечения заболеваний человека и животных |
| RU2693484C1 (ru) | 2013-11-22 | 2019-07-03 | СиЭль БАЙОСАЕНСИЗ ЭлЭлСи | Антагонисты гастрина для лечения и профилактики остеопороза |
| KR102408261B1 (ko) | 2014-02-03 | 2022-06-10 | 비타이 파마슈티컬즈, 엘엘씨 | Ror-감마의 디하이드로피롤로피리딘 저해제 |
| UA118989C2 (uk) | 2014-10-14 | 2019-04-10 | Вітае Фармасьютікалс, Інк. | Дигідропіролопіридинові інгібітори ror-гамма |
| US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
| US9845308B2 (en) | 2014-11-05 | 2017-12-19 | Vitae Pharmaceuticals, Inc. | Isoindoline inhibitors of ROR-gamma |
| US10251395B2 (en) | 2015-07-24 | 2019-04-09 | Bayer Cropscience Aktiengesellschaft | Substituted furano-/thienocycloalkylamino-2-pyrimidine derivatives and use thereof for controlling undesired plant growth |
| EP3331876B1 (en) | 2015-08-05 | 2020-10-07 | Vitae Pharmaceuticals, LLC | Modulators of ror-gamma |
| KR20180086221A (ko) | 2015-11-20 | 2018-07-30 | 비타이 파마슈티컬즈, 인코포레이티드 | Ror-감마의 조절물질 |
| TWI757266B (zh) | 2016-01-29 | 2022-03-11 | 美商維它藥物有限責任公司 | ＲＯＲ－γ調節劑 |
| US9481674B1 (en) | 2016-06-10 | 2016-11-01 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
| KR20240097982A (ko) | 2017-05-23 | 2024-06-27 | 메이 파마, 아이엔씨. | 병용 요법 |
| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| IL298639A (en) | 2017-07-24 | 2023-01-01 | Vitae Pharmaceuticals Llc | Inhibitors of gamma ror |
| MA49921A (fr) | 2017-08-14 | 2021-05-12 | Mei Pharma Inc | Polythérapie |
| TWI873290B (zh) | 2020-02-13 | 2025-02-21 | 德商百靈佳殷格翰國際股份有限公司 | 作為血漿激肽釋放酶抑制劑之雜芳族甲醯胺衍生物 |
| IL317728A (en) * | 2022-06-30 | 2025-02-01 | Adama Agan Ltd | Process for preparing biguanide and triazine salts |
| WO2025140655A1 (en) * | 2023-12-30 | 2025-07-03 | Fujian Haixi Pharmaceuticals Co., Ltd. | Heteroaryl compounds as multi-target protein kinase inhibitors |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932167A (en) | 1972-10-27 | 1976-01-13 | American Cyanamid Company | Substituted s-triazines as herbicidal agents |
| US3816419A (en) | 1972-10-27 | 1974-06-11 | American Cyanamid Co | Substituted s-triazines |
| US3953606A (en) | 1974-02-07 | 1976-04-27 | American Cyanamid Company | Compositions and method of using ureidotetralin compounds or derivatives thereof |
| US3953506A (en) | 1974-02-07 | 1976-04-27 | American Cyanamid Company | Ureidotetralin compounds |
| GB1479544A (en) * | 1974-02-07 | 1977-07-13 | American Cyanamid Co | 1,2,3,4-tetrahydro-1-naphthylurea derivatives their preparation and their use |
| US4156670A (en) * | 1976-03-23 | 1979-05-29 | American Cyanamid Company | Substituted tetrahydrobenzothiophenes and method of preparation thereof |
| EP0283522B1 (en) | 1986-09-30 | 1991-02-27 | Idemitsu Kosan Company Limited | Triazine derivative, production thereof, and herbicide containing same as effective ingredient |
| WO1990009378A1 (en) | 1989-02-20 | 1990-08-23 | Idemitsu Kosan Co. Ltd. | Triazine derivative and herbicide containing the same as active ingredient |
| US5286905A (en) | 1990-12-28 | 1994-02-15 | Idemitsu Kosan Company Limited | Process for producing biguanide derivative |
| US5250686A (en) | 1991-04-18 | 1993-10-05 | Idemitsu Kosan Company Limited | Process for producing triazine compounds |
| DE69405502T2 (de) * | 1993-04-08 | 1998-01-15 | Idemitsu Kosan Co | Verfahren zur herstellung von 2-fluor isobuttersäure und deren ester |
| JPH08183781A (ja) | 1994-12-28 | 1996-07-16 | Idemitsu Kosan Co Ltd | トリアジン誘導体およびそれを有効成分とする除草剤 |
| AU6242896A (en) * | 1995-11-27 | 1997-06-19 | Idemitsu Kosan Co. Ltd | Triazine derivatives |
| DE19607450A1 (de) * | 1996-02-28 | 1997-09-04 | Hoechst Schering Agrevo Gmbh | 2-Amino-4-bicycloamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| DE19641692A1 (de) * | 1996-10-10 | 1998-04-23 | Bayer Ag | Substituierte 2,4-Diamino-1,3,5-triazine |
| DE19744232A1 (de) * | 1997-10-07 | 1999-04-08 | Bayer Ag | Substituierte 2,4-Diamino-1,3,5-triazine |
| DE19921883A1 (de) | 1999-05-12 | 2000-11-16 | Bayer Ag | Substituierte Thienocycloalk(en)ylamino-1,3,5-triazine |
| CA2386218A1 (en) * | 1999-10-07 | 2001-04-12 | Amgen Inc. | Triazine kinase inhibitors |
-
2002
- 2002-02-20 DE DE10207037A patent/DE10207037A1/de not_active Withdrawn
-
2003
- 2003-02-06 MX MXPA04008044A patent/MXPA04008044A/es active IP Right Grant
- 2003-02-06 NZ NZ534737A patent/NZ534737A/xx unknown
- 2003-02-06 RU RU2004127931/04A patent/RU2004127931A/ru not_active Application Discontinuation
- 2003-02-06 ES ES03708083T patent/ES2312754T3/es not_active Expired - Lifetime
- 2003-02-06 EP EP03708083A patent/EP1478628B1/de not_active Expired - Lifetime
- 2003-02-06 BR BRPI0307877-9A patent/BR0307877B1/pt active IP Right Grant
- 2003-02-06 AT AT03708083T patent/ATE410416T1/de not_active IP Right Cessation
- 2003-02-06 JP JP2003569617A patent/JP4755396B2/ja not_active Expired - Lifetime
- 2003-02-06 AU AU2003212235A patent/AU2003212235A1/en not_active Abandoned
- 2003-02-06 WO PCT/EP2003/001157 patent/WO2003070710A1/de not_active Ceased
- 2003-02-06 KR KR1020047013035A patent/KR101107877B1/ko not_active Expired - Fee Related
- 2003-02-06 CA CA2476828A patent/CA2476828C/en not_active Expired - Fee Related
- 2003-02-06 DE DE50310607T patent/DE50310607D1/de not_active Expired - Lifetime
- 2003-02-06 CN CNB038042738A patent/CN100491359C/zh not_active Expired - Lifetime
- 2003-02-18 US US10/368,856 patent/US7479471B2/en not_active Expired - Lifetime
- 2003-02-18 TW TW092103329A patent/TW200303170A/zh unknown
- 2003-02-18 AR ARP030100526A patent/AR038562A1/es unknown
- 2003-02-19 MY MYPI20030581A patent/MY138410A/en unknown
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2004
- 2004-07-16 ZA ZA200405699A patent/ZA200405699B/en unknown
-
2009
- 2009-12-23 AU AU2009251129A patent/AU2009251129B9/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04008044A (es) | 2004-11-26 |
| KR101107877B1 (ko) | 2012-01-25 |
| WO2003070710A1 (de) | 2003-08-28 |
| EP1478628B1 (de) | 2008-10-08 |
| CN1636001A (zh) | 2005-07-06 |
| CN100491359C (zh) | 2009-05-27 |
| KR20040089655A (ko) | 2004-10-21 |
| US7479471B2 (en) | 2009-01-20 |
| AU2009251129B9 (en) | 2012-05-03 |
| NZ534737A (en) | 2006-03-31 |
| AU2003212235A1 (en) | 2003-09-09 |
| ATE410416T1 (de) | 2008-10-15 |
| ZA200405699B (en) | 2005-07-01 |
| CA2476828C (en) | 2012-08-21 |
| BR0307877A (pt) | 2004-12-28 |
| JP4755396B2 (ja) | 2011-08-24 |
| MY138410A (en) | 2009-05-29 |
| DE10207037A1 (de) | 2003-08-28 |
| AU2009251129B2 (en) | 2011-12-22 |
| AU2009251129A1 (en) | 2010-01-21 |
| EP1478628A1 (de) | 2004-11-24 |
| JP2005525351A (ja) | 2005-08-25 |
| AR038562A1 (es) | 2005-01-19 |
| BR0307877B1 (pt) | 2014-12-23 |
| ES2312754T3 (es) | 2009-03-01 |
| DE50310607D1 (de) | 2008-11-20 |
| RU2004127931A (ru) | 2005-04-10 |
| CA2476828A1 (en) | 2003-08-28 |
| US20040002424A1 (en) | 2004-01-01 |
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