BR112018008597B1 - Composto, composições herbicidas, mistura herbicida e método para o controle do crescimento de vegetação indesejada - Google Patents
Composto, composições herbicidas, mistura herbicida e método para o controle do crescimento de vegetação indesejada Download PDFInfo
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- BR112018008597B1 BR112018008597B1 BR112018008597-9A BR112018008597A BR112018008597B1 BR 112018008597 B1 BR112018008597 B1 BR 112018008597B1 BR 112018008597 A BR112018008597 A BR 112018008597A BR 112018008597 B1 BR112018008597 B1 BR 112018008597B1
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- Prior art keywords
- alkyl
- haloalkyl
- compound
- cycloalkyl
- alkoxyalkyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 127
- 238000000034 method Methods 0.000 title claims abstract description 61
- 239000004009 herbicide Substances 0.000 title claims abstract description 47
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 45
- 230000012010 growth Effects 0.000 title claims abstract description 12
- 239000002361 compost Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 304
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 16
- -1 4-isoquinolinyl Chemical group 0.000 claims description 160
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 90
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 87
- 125000001188 haloalkyl group Chemical group 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 70
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 64
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 55
- 239000003112 inhibitor Substances 0.000 claims description 52
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 36
- 239000007787 solid Substances 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 31
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 29
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 239000004480 active ingredient Substances 0.000 claims description 27
- 239000003085 diluting agent Substances 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 15
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 13
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 13
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 10
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 229930192334 Auxin Natural products 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 239000002363 auxin Substances 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 8
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 8
- 108010018763 Biotin carboxylase Proteins 0.000 claims description 8
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 8
- 108010001545 phytoene dehydrogenase Proteins 0.000 claims description 8
- 239000003223 protective agent Substances 0.000 claims description 8
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims description 7
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 claims description 7
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 claims description 7
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 claims description 7
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 7
- 102000005396 glutamine synthetase Human genes 0.000 claims description 7
- 108020002326 glutamine synthetase Proteins 0.000 claims description 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 6
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 6
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 6
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 108010060806 Photosystem II Protein Complex Proteins 0.000 claims description 6
- IGMNYECMUMZDDF-UHFFFAOYSA-N homogentisic acid Chemical compound OC(=O)CC1=CC(O)=CC=C1O IGMNYECMUMZDDF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 5
- 230000008166 cellulose biosynthesis Effects 0.000 claims description 5
- 239000011814 protection agent Substances 0.000 claims description 5
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 239000005644 Dazomet Substances 0.000 claims description 4
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 4
- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002169 Metam Substances 0.000 claims description 4
- 239000005643 Pelargonic acid Substances 0.000 claims description 4
- 108010081996 Photosystem I Protein Complex Proteins 0.000 claims description 4
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 claims description 4
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims description 4
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- 108010020183 3-phosphoshikimate 1-carboxyvinyltransferase Proteins 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000000394 mitotic effect Effects 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- RFZZKBWDDKMWNM-GTBMBKLPSA-N (5s,7r,8s,9r)-8,9-dihydroxy-7-(hydroxymethyl)-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@]11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-GTBMBKLPSA-N 0.000 claims description 2
- RFZZKBWDDKMWNM-UHFFFAOYSA-N Hydantocidin Natural products OC1C(O)C(CO)OC11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-UHFFFAOYSA-N 0.000 claims description 2
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 2
- QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 claims 1
- 101000813110 Mus musculus Elongation of very long chain fatty acids protein 6 Proteins 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 82
- 241000196324 Embryophyta Species 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- 239000002904 solvent Substances 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000002131 composite material Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 125000001424 substituent group Chemical group 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- 239000003153 chemical reaction reagent Substances 0.000 description 25
- 238000009472 formulation Methods 0.000 description 25
- 239000002585 base Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 125000005843 halogen group Chemical group 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Inorganic materials [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 15
- 239000011701 zinc Substances 0.000 description 15
- 150000002148 esters Chemical group 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 235000013311 vegetables Nutrition 0.000 description 14
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 10
- 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 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
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- 238000011282 treatment Methods 0.000 description 10
- 229910052725 zinc Inorganic materials 0.000 description 10
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
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- 235000011152 sodium sulphate Nutrition 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
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- 239000007832 Na2SO4 Substances 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
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- 229910052763 palladium Inorganic materials 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
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- 125000003282 alkyl amino group Chemical group 0.000 description 6
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000007819 coupling partner Substances 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 6
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- C07D405/10—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 carbon chain containing aromatic rings
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- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/10—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 carbon chain containing aromatic rings
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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| US201562247585P | 2015-10-28 | 2015-10-28 | |
| US62/247,585 | 2015-10-28 | ||
| PCT/US2016/058762 WO2017074992A1 (en) | 2015-10-28 | 2016-10-26 | Novel pyrdazinone herbicides |
Publications (2)
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| BR112018008597A2 BR112018008597A2 (pt) | 2019-04-24 |
| BR112018008597B1 true BR112018008597B1 (pt) | 2022-03-03 |
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| EP (1) | EP3368523B1 (https=) |
| JP (1) | JP6905521B2 (https=) |
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| BR (1) | BR112018008597B1 (https=) |
| CA (1) | CA3003419C (https=) |
| RU (1) | RU2764746C2 (https=) |
| WO (1) | WO2017074992A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10118917B2 (en) | 2014-04-29 | 2018-11-06 | E I Du Pont De Nemours And Company | Pyridazinone herbicides |
| TWI785022B (zh) * | 2017-03-28 | 2022-12-01 | 美商富曼西公司 | 新穎噠嗪酮類除草劑 |
| BR112019028016B1 (pt) | 2017-06-30 | 2023-12-05 | Fmc Corporation | Composto, composições herbicidas, mistura herbicida e método para controlar o crescimento de vegetação indesejada |
| CN112789266A (zh) * | 2018-09-27 | 2021-05-11 | Fmc公司 | 用于制备除草剂哒嗪酮的中间体 |
| UA129288C2 (uk) | 2018-09-27 | 2025-03-12 | ЕфЕмСі КОРПОРЕЙШН | Піридазинонові гербіциди і піридазинонові проміжні продукти, які використовуються для отримання гербіциду |
| KR20210145788A (ko) | 2019-04-01 | 2021-12-02 | 닛산 가가쿠 가부시키가이샤 | 피리다지논 화합물 및 제초제 |
| KR20220070430A (ko) * | 2019-09-25 | 2022-05-31 | 닛뽕소다 가부시키가이샤 | 피리다진 화합물 및 제초제 |
| MX2023007412A (es) * | 2020-12-22 | 2023-06-29 | Fmc Corp | Herbicidas de tipo piridazinona sustituida. |
| CN116635386A (zh) * | 2020-12-22 | 2023-08-22 | Fmc公司 | 取代的哒嗪酮除草剂 |
| AR125453A1 (es) | 2021-04-27 | 2023-07-19 | Bayer Ag | Piridazinonas sustituidas, sales o n-óxidos de las mismas y su uso como sustancias herbicidamente activas |
| KR20240168370A (ko) * | 2022-03-30 | 2024-11-29 | 이시하라 산교 가부시끼가이샤 | 피리다지논계 화합물 또는 그의 염 및 그들을 함유하는 유해 생물 방제제 |
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2016
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- 2016-10-26 RU RU2018115985A patent/RU2764746C2/ru active
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- 2016-10-26 WO PCT/US2016/058762 patent/WO2017074992A1/en not_active Ceased
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| CA3003419C (en) | 2023-01-24 |
| AR106521A1 (es) | 2018-01-24 |
| JP6905521B2 (ja) | 2021-07-21 |
| WO2017074992A1 (en) | 2017-05-04 |
| CA3003419A1 (en) | 2017-05-04 |
| CN108495849A (zh) | 2018-09-04 |
| RU2018115985A (ru) | 2019-11-28 |
| US10750743B2 (en) | 2020-08-25 |
| AU2016346303B2 (en) | 2021-01-07 |
| EP3368523B1 (en) | 2021-07-14 |
| AU2016346303A1 (en) | 2018-05-10 |
| RU2764746C2 (ru) | 2022-01-20 |
| BR112018008597A2 (pt) | 2019-04-24 |
| RU2018115985A3 (https=) | 2020-03-10 |
| CN108495849B (zh) | 2020-11-10 |
| JP2018533577A (ja) | 2018-11-15 |
| EP3368523A1 (en) | 2018-09-05 |
| US20180332851A1 (en) | 2018-11-22 |
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Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 26/10/2016, OBSERVADAS AS CONDICOES LEGAIS. |