MXPA04008044A - 2-amino-4-biciclilamino-6h-1,3,5-triazinas, procedimientos para su preparacion y su utilizacion como agentes herbicidas y reguladores del crecimiento de las plantas. - Google Patents
2-amino-4-biciclilamino-6h-1,3,5-triazinas, procedimientos para su preparacion y su utilizacion como agentes herbicidas y reguladores del crecimiento de las plantas.Info
- Publication number
- MXPA04008044A MXPA04008044A MXPA04008044A MXPA04008044A MXPA04008044A MX PA04008044 A MXPA04008044 A MX PA04008044A MX PA04008044 A MXPA04008044 A MX PA04008044A MX PA04008044 A MXPA04008044 A MX PA04008044A MX PA04008044 A MXPA04008044 A MX PA04008044A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- carbonyl
- alkoxy
- amino
- crc4
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 239000004009 herbicide Substances 0.000 title claims abstract description 36
- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title description 7
- MRJTXIONCKEJGN-UHFFFAOYSA-N 1,4-dihydro-1,3,5-triazin-2-amine Chemical class NC1=NC=NCN1 MRJTXIONCKEJGN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 144
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 377
- -1 alkyl radical Chemical class 0.000 claims description 330
- 150000003254 radicals Chemical class 0.000 claims description 273
- 125000003545 alkoxy group Chemical group 0.000 claims description 207
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 132
- 229910052736 halogen Inorganic materials 0.000 claims description 107
- 150000002367 halogens Chemical class 0.000 claims description 107
- 125000004432 carbon atom Chemical group C* 0.000 claims description 101
- 125000001188 haloalkyl group Chemical group 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
- 125000000623 heterocyclic group Chemical group 0.000 claims description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 69
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 68
- RFMQOHXWHFHOJF-UHFFFAOYSA-N cyano thiocyanate Chemical compound N#CSC#N RFMQOHXWHFHOJF-UHFFFAOYSA-N 0.000 claims description 66
- 125000005842 heteroatom Chemical group 0.000 claims description 64
- 125000004122 cyclic group Chemical group 0.000 claims description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims description 54
- 125000003342 alkenyl group Chemical group 0.000 claims description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 50
- 125000006413 ring segment Chemical group 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 229910052717 sulfur Inorganic materials 0.000 claims description 47
- 229910052760 oxygen Inorganic materials 0.000 claims description 46
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 37
- 125000000304 alkynyl group Chemical group 0.000 claims description 36
- 125000001589 carboacyl group Chemical group 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 31
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000002015 acyclic group Chemical group 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 24
- 238000009472 formulation Methods 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 23
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 23
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000002837 carbocyclic group Chemical group 0.000 claims description 20
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 12
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 12
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 11
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 10
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 7
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 6
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 5
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 230000008635 plant growth Effects 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 3
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 3
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 229940123208 Biguanide Drugs 0.000 claims description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- BWOVZCWSJFYBRM-UHFFFAOYSA-N carbononitridic isocyanate Chemical compound O=C=NC#N BWOVZCWSJFYBRM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006805 (C3-C9) cycloalkylamino group Chemical group 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 claims 1
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 150000002905 orthoesters Chemical class 0.000 claims 1
- 230000026267 regulation of growth Effects 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 abstract description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 229
- 241000196324 Embryophyta Species 0.000 description 99
- 239000013543 active substance Substances 0.000 description 40
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 28
- 239000000729 antidote Substances 0.000 description 26
- 239000002585 base Substances 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000000575 pesticide Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 230000002363 herbicidal effect Effects 0.000 description 20
- 239000000126 substance Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000008187 granular material Substances 0.000 description 16
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 16
- 230000009261 transgenic effect Effects 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 240000007594 Oryza sativa Species 0.000 description 15
- 235000007164 Oryza sativa Nutrition 0.000 description 15
- 235000009566 rice Nutrition 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
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- 125000004494 ethyl ester group Chemical group 0.000 description 10
- 239000008259 solid foam Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 9
- 239000000645 desinfectant Substances 0.000 description 9
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- 125000004043 oxo group Chemical group O=* 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- 244000062793 Sorghum vulgare Species 0.000 description 8
- 150000001342 alkaline earth metals Chemical class 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
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- 125000005843 halogen group Chemical group 0.000 description 7
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 7
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- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 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
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 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
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation 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
- WEWFIUPOLKEEJP-UHFFFAOYSA-N triazine-4,6-diamine Chemical compound NC1=CC(N)=NN=N1 WEWFIUPOLKEEJP-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
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical compound COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000009105 vegetative growth Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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
Landscapes
- 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 (2)
| 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 |
| PCT/EP2003/001157 WO2003070710A1 (de) | 2002-02-20 | 2003-02-06 | 2-amino-4-bicyclylamino-6h-1,3,5-triazine, verfahren zu deren herstellung und deren verwendung als herbizide und pflanzenwachstumsregulatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04008044A true MXPA04008044A (es) | 2004-11-26 |
Family
ID=27635161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04008044A MXPA04008044A (es) | 2002-02-20 | 2003-02-06 | 2-amino-4-biciclilamino-6h-1,3,5-triazinas, procedimientos para su preparacion y su utilizacion como agentes herbicidas y reguladores del crecimiento de las plantas. |
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 |
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| 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
-
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 |
|---|---|
| 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 |
| TW200303170A (en) | 2003-09-01 |
| 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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