BG64096B1 - 2-амино-4-бициклоамино-1,3,5-триазини като хербициди и растежни регулатори на растенията - Google Patents
2-амино-4-бициклоамино-1,3,5-триазини като хербициди и растежни регулатори на растенията Download PDFInfo
- Publication number
- BG64096B1 BG64096B1 BG102706A BG10270698A BG64096B1 BG 64096 B1 BG64096 B1 BG 64096B1 BG 102706 A BG102706 A BG 102706A BG 10270698 A BG10270698 A BG 10270698A BG 64096 B1 BG64096 B1 BG 64096B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- alkyl
- group
- carbonyl
- alkoxy
- substituted
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims description 13
- 239000005648 plant growth regulator Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 375
- -1 cyano, thiocyanato Chemical group 0.000 claims description 137
- 125000000623 heterocyclic group Chemical group 0.000 claims description 81
- 229910052736 halogen Inorganic materials 0.000 claims description 78
- 150000002367 halogens Chemical class 0.000 claims description 76
- 125000001424 substituent group Chemical group 0.000 claims description 71
- 125000003545 alkoxy group Chemical group 0.000 claims description 60
- 125000005842 heteroatom Chemical group 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 125000003342 alkenyl group Chemical group 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 125000006413 ring segment Chemical group 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 125000004414 alkyl thio group Chemical group 0.000 claims description 38
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 150000003254 radicals Chemical class 0.000 claims description 37
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 35
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 125000004122 cyclic group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 32
- 150000002431 hydrogen Chemical class 0.000 claims description 31
- 125000003282 alkyl amino group Chemical group 0.000 claims description 27
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- 125000002015 acyclic group Chemical group 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 230000012010 growth Effects 0.000 claims description 12
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 230000002363 herbicidal effect Effects 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
- 239000002689 soil Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 5
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 5
- 229940123208 Biguanide Drugs 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000013543 active substance Substances 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000009472 formulation Methods 0.000 description 19
- 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 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
- 239000003513 alkali Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 10
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 150000004678 hydrides Chemical class 0.000 description 9
- 150000004679 hydroxides Chemical class 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000004562 water dispersible granule Substances 0.000 description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000003460 sulfonic acids Chemical class 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000010410 dusting Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 241000234653 Cyperus Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000612182 Rexea solandri Species 0.000 description 3
- 235000005775 Setaria Nutrition 0.000 description 3
- 241000232088 Setaria <nematode> Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 3
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 description 2
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- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 235000006463 Brassica alba Nutrition 0.000 description 2
- 244000140786 Brassica hirta Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- 244000144786 Chrysanthemum segetum Species 0.000 description 2
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 2
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- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 240000008114 Panicum miliaceum Species 0.000 description 2
- 235000007199 Panicum miliaceum Nutrition 0.000 description 2
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 2
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- 235000007238 Secale cereale Nutrition 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
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- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-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
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 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
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 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
- 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
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 239000004550 soluble concentrate 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
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 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
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-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
- 125000001544 thienyl group Chemical group 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
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 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
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 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
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-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
- 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
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 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
- 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
-
- 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
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
-
- 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- 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
- 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
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19607450A DE19607450A1 (de) | 1996-02-28 | 1996-02-28 | 2-Amino-4-bicycloamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| PCT/EP1997/000702 WO1997031904A1 (fr) | 1996-02-28 | 1997-02-14 | 2-amino-4-bicycloamino-1,3,5-triazines s'utilisant comme herbicides et regulateurs de croissance vegetale |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG102706A BG102706A (en) | 1999-04-30 |
| BG64096B1 true BG64096B1 (bg) | 2003-12-31 |
Family
ID=7786633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG102706A BG64096B1 (bg) | 1996-02-28 | 1998-08-20 | 2-амино-4-бициклоамино-1,3,5-триазини като хербициди и растежни регулатори на растенията |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6069114A (fr) |
| EP (1) | EP0885201A1 (fr) |
| JP (1) | JP4442931B2 (fr) |
| KR (1) | KR100849899B1 (fr) |
| CN (1) | CN1083439C (fr) |
| AU (1) | AU714187B2 (fr) |
| BG (1) | BG64096B1 (fr) |
| BR (1) | BR9707781B1 (fr) |
| CA (1) | CA2248338C (fr) |
| CL (1) | CL2004001102A1 (fr) |
| CZ (1) | CZ296253B6 (fr) |
| DE (1) | DE19607450A1 (fr) |
| HU (1) | HUP9901113A3 (fr) |
| ID (1) | ID16056A (fr) |
| MX (1) | MX9807064A (fr) |
| MY (1) | MY118281A (fr) |
| PL (1) | PL195265B1 (fr) |
| RU (1) | RU2314297C2 (fr) |
| TR (1) | TR199801714T2 (fr) |
| TW (1) | TW368395B (fr) |
| UA (1) | UA58505C2 (fr) |
| WO (1) | WO1997031904A1 (fr) |
| ZA (1) | ZA971642B (fr) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9611570A (pt) * | 1995-11-27 | 1999-03-30 | Idemitsu Kosan Co | Derivados de triazina |
| DE19830902A1 (de) | 1998-07-10 | 2000-01-13 | Hoechst Schering Agrevo Gmbh | Verfahren zur Herstellung von 2-Amino-4-chlor-1,3,5-triazinen |
| DE19842894A1 (de) * | 1998-09-18 | 2000-03-23 | Hoechst Schering Agrevo Gmbh | Synergistische Wirkstoffkombinationen zur Bekämpfung von Schadpflanzen in Nutzpflanzenkulturen |
| DE19921883A1 (de) * | 1999-05-12 | 2000-11-16 | Bayer Ag | Substituierte Thienocycloalk(en)ylamino-1,3,5-triazine |
| JP2001151612A (ja) * | 1999-09-09 | 2001-06-05 | Nippon Bayer Agrochem Co Ltd | 除草性1,3,5−トリアジン類 |
| GB0026010D0 (en) * | 2000-10-24 | 2000-12-13 | Air Prod & Chem | N-fluorotriazinium fluorinating agents |
| GB0026012D0 (en) | 2000-10-24 | 2000-12-13 | Air Prod & Chem | Electrophilic fluorination |
| EP2206703A1 (fr) * | 2008-12-30 | 2010-07-14 | Bayer CropScience AG | Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes |
| DE10207037A1 (de) * | 2002-02-20 | 2003-08-28 | Bayer Cropscience Gmbh | 2-Amino-4-bicyclyamino-6H-1,3.5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| ES2466245T3 (es) | 2003-02-05 | 2014-06-09 | Bayer Cropscience Ag | Amino-1,3,5-triazinas N-sustituidas con radicales bicíclicos quirales, procedimiento para su preparación, composiciones de las mismas y su uso como herbicidas y reguladores del crecimiento de las plantas |
| DE102004034571A1 (de) * | 2004-07-17 | 2006-02-23 | Bayer Cropscience Gmbh | Herbizide Mittel |
| EP1836894A1 (fr) | 2006-03-25 | 2007-09-26 | Bayer CropScience GmbH | Nouvelles formulations solides à base de sulfonamides |
| EP1790227A1 (fr) * | 2005-11-25 | 2007-05-30 | Bayer CropScience AG | Suspensions aqueuses concentrées renferment des herbicides du group des 2,4-diamino-s-triazines |
| EP1854355A1 (fr) * | 2006-03-15 | 2007-11-14 | Bayer CropScience AG | Suspensions aqueuses concentrées |
| EP1844654A1 (fr) | 2006-03-29 | 2007-10-17 | Bayer CropScience GmbH | Activateur de la pénétration foliaire des principes actives agrochimiques |
| DE102007013362A1 (de) | 2007-03-16 | 2008-09-18 | Bayer Cropscience Ag | Penetrationsförderer für herbizide Wirkstoffe |
| 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 |
| DE102006016885A1 (de) * | 2006-04-11 | 2007-10-18 | Bayer Cropscience Ag | Mit bicyclischen Radikalen N-substituierte Diamino-1,3,5-triazine, Verfahren für ihre Herstellung, Zubereitungen davon und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| DE102006059941A1 (de) | 2006-12-19 | 2008-06-26 | Bayer Cropscience Ag | Substituierte 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| EP1958509A1 (fr) * | 2007-02-19 | 2008-08-20 | Bayer CropScience AG | Combinaison d'herbicides |
| EP2092825A1 (fr) * | 2008-02-21 | 2009-08-26 | Bayer CropScience Aktiengesellschaft | Combinaison herbicide contenant un herbicide de la classe des diamino-s-triazines |
| EP2147600A1 (fr) * | 2008-07-21 | 2010-01-27 | Bayer CropScience AG | Procédé de désherbage de gazon |
| EP2210879A1 (fr) * | 2008-12-30 | 2010-07-28 | Bayer CropScience AG | Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes |
| WO2011076731A1 (fr) | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Formulation liquide de 2-iodo-n-[(4-méthoxy-6-méthyl-1, 3, 5-triazin-2-yl) carbamoyl] benzène sulfonamide |
| ES2649937T3 (es) | 2010-12-21 | 2018-01-16 | Bayer Cropscience Lp | Mutantes tipo papel de lija de Bacillus y procedimientos de uso de los mismos para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas |
| BR112014005654A2 (pt) | 2011-09-12 | 2017-03-28 | Bayer Cropscience Lp | métodos para melhorar a saúde e promover o crescimento de uma planta e/ou de melhorar o amadurecimento da fruta |
| WO2015007711A1 (fr) * | 2013-07-16 | 2015-01-22 | Basf Se | Azines herbicides |
| EP2930174A1 (fr) * | 2014-04-07 | 2015-10-14 | Basf Se | Dérivés de diaminotriazine en tant qu'herbicides |
| WO2015155129A1 (fr) * | 2014-04-07 | 2015-10-15 | Basf Se | Composé de diaminotriazine |
| MX379428B (es) * | 2014-04-23 | 2025-03-10 | Basf Se | Compuesto de diaminotriazina como herbicidas. |
| KR101630161B1 (ko) * | 2014-07-25 | 2016-06-14 | 한국화학연구원 | 열안정성이 우수한 탄성 폴리우레탄의 중합 방법 및 이로부터 제조된 탄성 폴리우레탄 중합체 |
| CN107105658A (zh) | 2014-11-18 | 2017-08-29 | 拜耳作物科学股份公司 | 某些除草剂结合物在块根作物植物中的用途 |
| BR112017023253B1 (pt) | 2015-04-27 | 2022-09-13 | Basf Se | Combinações de herbicida que compreendem glufosinato e indaziflam |
| UA124491C2 (uk) | 2015-05-11 | 2021-09-29 | Баєр Кропсаєнс Акціенгезельшафт | Комбінації гербіцидів, які містять l-глюфосинат та індазифлам |
| WO2018104142A1 (fr) | 2016-12-07 | 2018-06-14 | Bayer Cropscience Aktiengesellschaft | Combinaison herbicide contenant de la triafamone et de l'indaziflame |
| WO2018184978A1 (fr) * | 2017-04-05 | 2018-10-11 | Bayer Cropscience Aktiengesellschaft | Dérivés de 2-amino-5-oxyalkyl-pyrimidine et leur utilisation pour lutter contre la croissance de plantes adventices |
| BR112020011214A2 (pt) * | 2017-12-04 | 2020-11-17 | Bayer Cropscience Aktiengesellschaft | derivados de 3-amino-[1,2,4]-triazol e seu uso para controlar o crescimento indesejado de plantas. |
| CA3179690A1 (fr) | 2020-04-09 | 2021-10-14 | Bayer Aktiengesellschaft | Combinaison de composes ayant une activite herbicide superieure |
| WO2021204862A1 (fr) | 2020-04-09 | 2021-10-14 | Bayer Aktiengesellschaft | Combinaison de composés ayant une activité herbicide supérieure |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3816419A (en) * | 1972-10-27 | 1974-06-11 | American Cyanamid Co | Substituted s-triazines |
| US3932167A (en) * | 1972-10-27 | 1976-01-13 | American Cyanamid Company | Substituted s-triazines as herbicidal agents |
| WO1988002368A1 (fr) * | 1986-09-30 | 1988-04-07 | Idemitsu Kosan Company Limited | Derive de triazine, production de ce derive, et herbicide le contenant en tant que principe actif |
| US4932998A (en) * | 1986-09-30 | 1990-06-12 | Idemitsu Kosan Company Limited | Triazine derivatives, and herbicides comprising the same as the effective ingredient |
| KR940001728B1 (ko) * | 1989-02-20 | 1994-03-05 | 이데미쓰 고산 가부시끼가이샤 | 트리아진 유도체 및 그것을 유효성분으로 하는 제초제 |
| 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 |
| WO1994024086A1 (fr) * | 1993-04-08 | 1994-10-27 | Idemitsu Kosan Co., Ltd. | Procede pour produire de l'acide 2-fluoro-isobutyrique ou un ester de celui-ci |
| 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 |
| DE19522137A1 (de) * | 1995-06-19 | 1997-01-02 | Hoechst Schering Agrevo Gmbh | 2-Amino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
-
1996
- 1996-02-28 DE DE19607450A patent/DE19607450A1/de not_active Withdrawn
-
1997
- 1997-02-14 EP EP97903284A patent/EP0885201A1/fr not_active Ceased
- 1997-02-14 PL PL97328660A patent/PL195265B1/pl unknown
- 1997-02-14 JP JP53054497A patent/JP4442931B2/ja not_active Expired - Lifetime
- 1997-02-14 CZ CZ0276198A patent/CZ296253B6/cs not_active IP Right Cessation
- 1997-02-14 HU HU9901113A patent/HUP9901113A3/hu not_active Application Discontinuation
- 1997-02-14 TR TR1998/01714T patent/TR199801714T2/xx unknown
- 1997-02-14 WO PCT/EP1997/000702 patent/WO1997031904A1/fr not_active Application Discontinuation
- 1997-02-14 AU AU17693/97A patent/AU714187B2/en not_active Expired
- 1997-02-14 CA CA002248338A patent/CA2248338C/fr not_active Expired - Lifetime
- 1997-02-14 UA UA98095076A patent/UA58505C2/uk unknown
- 1997-02-14 KR KR1019980706747A patent/KR100849899B1/ko not_active Expired - Lifetime
- 1997-02-14 RU RU98117853/04A patent/RU2314297C2/ru active
- 1997-02-14 CN CN97192683A patent/CN1083439C/zh not_active Expired - Lifetime
- 1997-02-14 BR BRPI9707781-0A patent/BR9707781B1/pt not_active IP Right Cessation
- 1997-02-25 US US08/805,576 patent/US6069114A/en not_active Expired - Lifetime
- 1997-02-26 ZA ZA9701642A patent/ZA971642B/xx unknown
- 1997-02-26 MY MYPI97000728A patent/MY118281A/en unknown
- 1997-02-26 TW TW086102346A patent/TW368395B/zh not_active IP Right Cessation
- 1997-02-27 ID IDP970588A patent/ID16056A/id unknown
-
1998
- 1998-08-20 BG BG102706A patent/BG64096B1/bg unknown
- 1998-08-28 MX MX9807064A patent/MX9807064A/es unknown
-
2004
- 2004-05-18 CL CL200401102A patent/CL2004001102A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2248338A1 (fr) | 1997-09-04 |
| RU2314297C2 (ru) | 2008-01-10 |
| PL195265B1 (pl) | 2007-08-31 |
| MY118281A (en) | 2004-09-30 |
| TR199801714T2 (xx) | 1998-12-21 |
| CZ296253B6 (cs) | 2006-02-15 |
| TW368395B (en) | 1999-09-01 |
| ZA971642B (en) | 1997-11-25 |
| MX9807064A (es) | 1998-12-31 |
| CN1212687A (zh) | 1999-03-31 |
| ID16056A (id) | 1997-08-28 |
| JP4442931B2 (ja) | 2010-03-31 |
| BR9707781A (pt) | 1999-07-27 |
| JP2000505462A (ja) | 2000-05-09 |
| US6069114A (en) | 2000-05-30 |
| AU714187B2 (en) | 1999-12-23 |
| AU1769397A (en) | 1997-09-16 |
| CL2004001102A1 (es) | 2005-04-29 |
| KR100849899B1 (ko) | 2010-06-15 |
| BG102706A (en) | 1999-04-30 |
| CA2248338C (fr) | 2008-09-02 |
| CN1083439C (zh) | 2002-04-24 |
| CZ276198A3 (cs) | 1998-12-16 |
| UA58505C2 (uk) | 2003-08-15 |
| WO1997031904A1 (fr) | 1997-09-04 |
| BR9707781B1 (pt) | 2010-10-05 |
| DE19607450A1 (de) | 1997-09-04 |
| HUP9901113A3 (en) | 2000-06-28 |
| KR19990087338A (ko) | 1999-12-27 |
| PL328660A1 (en) | 1999-02-15 |
| HUP9901113A1 (hu) | 1999-07-28 |
| EP0885201A1 (fr) | 1998-12-23 |
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