RU2750293C2 - Арилзамещенные бициклические соединения в качестве гербицидов - Google Patents
Арилзамещенные бициклические соединения в качестве гербицидов Download PDFInfo
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- RU2750293C2 RU2750293C2 RU2017134776A RU2017134776A RU2750293C2 RU 2750293 C2 RU2750293 C2 RU 2750293C2 RU 2017134776 A RU2017134776 A RU 2017134776A RU 2017134776 A RU2017134776 A RU 2017134776A RU 2750293 C2 RU2750293 C2 RU 2750293C2
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- 239000004009 herbicide Substances 0.000 title abstract description 36
- 125000002619 bicyclic group Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 327
- -1 3-trifluoromethylphenyl Chemical group 0.000 claims abstract description 210
- 239000000203 mixture Substances 0.000 claims abstract description 132
- 125000001424 substituent group Chemical group 0.000 claims abstract description 101
- 241000196324 Embryophyta Species 0.000 claims abstract description 99
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 53
- 150000002367 halogens Chemical class 0.000 claims abstract description 53
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 41
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 40
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 34
- 125000004429 atom Chemical group 0.000 claims abstract description 23
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 19
- 230000012010 growth Effects 0.000 claims abstract description 15
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 75
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 47
- 125000001188 haloalkyl group Chemical group 0.000 claims description 34
- 239000003085 diluting agent Substances 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 24
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 239000012634 fragment Substances 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 238000007363 ring formation reaction Methods 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- LYCRYYGXUAUVHL-UHFFFAOYSA-N N-(2-fluorophenyl)-6-[3-(trifluoromethyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole-7-carboxamide Chemical compound FC1=C(C=CC=C1)NC(=O)C1C(CN2C1=NN=C2)C1=CC(=CC=C1)C(F)(F)F LYCRYYGXUAUVHL-UHFFFAOYSA-N 0.000 claims description 4
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 claims description 4
- BJKHQBSYHJZIPH-UHFFFAOYSA-N N-(2-fluorophenyl)-3-oxo-6-[3-(trifluoromethyl)phenyl]-2,5,6,7-tetrahydropyrrolo[1,2-a]imidazole-7-carboxamide Chemical compound FC1=C(C=CC=C1)NC(=O)C1C(CN2C1=NCC2=O)C1=CC(=CC=C1)C(F)(F)F BJKHQBSYHJZIPH-UHFFFAOYSA-N 0.000 claims description 3
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 claims 1
- JRKYOVIBVMSBRP-UHFFFAOYSA-N OC(C(C(CN1)C2=CC=C(C(F)(F)F)C=C2)C1=O)=O Chemical compound OC(C(C(CN1)C2=CC=C(C(F)(F)F)C=C2)C1=O)=O JRKYOVIBVMSBRP-UHFFFAOYSA-N 0.000 claims 1
- BXBUVIPNRGDTNE-UHFFFAOYSA-N sodium;hydrobromide Chemical compound [Na].Br BXBUVIPNRGDTNE-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 44
- 239000000126 substance Substances 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 156
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 240000008042 Zea mays Species 0.000 description 50
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 49
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 46
- 235000009973 maize Nutrition 0.000 description 46
- 230000014509 gene expression Effects 0.000 description 42
- 239000003112 inhibitor Substances 0.000 description 41
- 229920000742 Cotton Polymers 0.000 description 40
- 241000219146 Gossypium Species 0.000 description 40
- 239000002904 solvent Substances 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 39
- 125000004122 cyclic group Chemical group 0.000 description 35
- 229910052739 hydrogen Inorganic materials 0.000 description 35
- 125000000623 heterocyclic group Chemical group 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 32
- 241001167018 Aroa Species 0.000 description 31
- 101100491986 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) aromA gene Proteins 0.000 description 31
- 101150037081 aroA gene Proteins 0.000 description 31
- 125000004093 cyano group Chemical group *C#N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- 235000006008 Brassica napus var napus Nutrition 0.000 description 29
- 150000003839 salts Chemical class 0.000 description 29
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 28
- 240000000385 Brassica napus var. napus Species 0.000 description 28
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 28
- 235000010469 Glycine max Nutrition 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 240000007594 Oryza sativa Species 0.000 description 26
- 235000007164 Oryza sativa Nutrition 0.000 description 26
- 239000004480 active ingredient Substances 0.000 description 26
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 25
- 235000009566 rice Nutrition 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 24
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 23
- 125000004430 oxygen atom Chemical group O* 0.000 description 23
- 125000004434 sulfur atom Chemical group 0.000 description 23
- 101100497219 Bacillus thuringiensis subsp. kurstaki cry1Ac gene Proteins 0.000 description 22
- 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 22
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000009472 formulation Methods 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 21
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 20
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 20
- 101150065438 cry1Ab gene Proteins 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 17
- 150000002148 esters Chemical group 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 16
- 125000000262 haloalkenyl group Chemical group 0.000 description 16
- 125000000232 haloalkynyl group Chemical group 0.000 description 16
- 125000005842 heteroatom Chemical group 0.000 description 16
- 125000004971 nitroalkyl group Chemical group 0.000 description 16
- 229910052708 sodium Inorganic materials 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 15
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 description 15
- 238000009835 boiling Methods 0.000 description 15
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 15
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 description 15
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 14
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 14
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 14
- 150000001721 carbon Chemical group 0.000 description 14
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 14
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 14
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 description 14
- 238000006467 substitution reaction Methods 0.000 description 14
- 238000012546 transfer Methods 0.000 description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 13
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 13
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 125000005347 halocycloalkyl group Chemical group 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 125000004665 trialkylsilyl group Chemical group 0.000 description 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 12
- 125000006815 (C4-C10) cycloalkylaminocarbonyl group Chemical group 0.000 description 12
- 125000006781 (C4-C10) cycloalkylcarbonyl group Chemical group 0.000 description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 11
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 229930192334 Auxin Natural products 0.000 description 10
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000729 antidote Substances 0.000 description 10
- 239000002363 auxin Substances 0.000 description 10
- 239000006184 cosolvent Substances 0.000 description 10
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 description 10
- 125000005366 cycloalkylthio group Chemical group 0.000 description 10
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YIEOMSIYLBLZAW-UHFFFAOYSA-N N-(2,3-difluorophenyl)-3-ethyl-6-[4-(trifluoromethyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole-7-carboxamide Chemical compound FC1=C(C=CC=C1F)NC(=O)C1C(CN2C1=NN=C2CC)C1=CC=C(C=C1)C(F)(F)F YIEOMSIYLBLZAW-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000003302 alkenyloxy group Chemical group 0.000 description 9
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 8
- 101150065749 Churc1 gene Proteins 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 102100038239 Protein Churchill Human genes 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 8
- 125000004438 haloalkoxy group Chemical group 0.000 description 8
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 8
- 125000004995 haloalkylthio group Chemical group 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 7
- 239000005562 Glyphosate Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 description 7
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 7
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 6
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 6
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 description 6
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 description 6
- KPSTXQYTZBZXMM-UHFFFAOYSA-N 2-[8-chloro-4-(4-methoxyphenyl)-3-oxoquinoxaline-2-carbonyl]cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C(=O)C2C(CCCC2=O)=O)=NC2=C(Cl)C=CC=C21 KPSTXQYTZBZXMM-UHFFFAOYSA-N 0.000 description 6
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 description 6
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 description 6
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 description 6
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 description 6
- 101100485131 Arabidopsis thaliana WRKY45 gene Proteins 0.000 description 6
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 6
- 108010018763 Biotin carboxylase Proteins 0.000 description 6
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 101100373131 Oryza sativa subsp. indica WRKY45-2 gene Proteins 0.000 description 6
- 101100049733 Oryza sativa subsp. japonica WRKY45-1 gene Proteins 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 235000021536 Sugar beet Nutrition 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 6
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 6
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 description 6
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- LLLFASISUZUJEQ-UHFFFAOYSA-N orbencarb Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1Cl LLLFASISUZUJEQ-UHFFFAOYSA-N 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000010653 organometallic reaction Methods 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- UCDPMNSCCRBWIC-UHFFFAOYSA-N orthosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)N(C)C)=N1 UCDPMNSCCRBWIC-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
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- 125000002255 pentenyl group Chemical class C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 1
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- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
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- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000243 photosynthetic effect Effects 0.000 description 1
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- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
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- 235000019448 polyvinylpyrrolidone-vinyl acetate copolymer Nutrition 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical class [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical class [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
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- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-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
- 238000001243 protein synthesis Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 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
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- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
- AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 1
- QGKPUZOFTJQTHL-UHFFFAOYSA-M sodium;4-cyano-2,6-diiodophenolate Chemical compound [Na+].[O-]C1=C(I)C=C(C#N)C=C1I QGKPUZOFTJQTHL-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 239000011877 solvent mixture Substances 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 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
- 238000007280 thionation reaction Methods 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 210000002377 thylakoid Anatomy 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 231100000765 toxin Toxicity 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
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- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
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- 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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 230000004222 uncontrolled growth Effects 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C07C205/53—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catching Or Destruction (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562160592P | 2015-05-12 | 2015-05-12 | |
| US62/160,592 | 2015-05-12 | ||
| PCT/US2016/030450 WO2016182780A1 (en) | 2015-05-12 | 2016-05-02 | Aryl substituted bicyclic compounds as herbicides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017134776A RU2017134776A (ru) | 2019-04-09 |
| RU2017134776A3 RU2017134776A3 (enExample) | 2019-09-30 |
| RU2750293C2 true RU2750293C2 (ru) | 2021-06-25 |
Family
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| JP6524086B2 (ja) | 2013-12-03 | 2019-06-05 | エフ エム シー コーポレーションFmc Corporation | ピロリジノン除草剤 |
| US11589583B2 (en) | 2013-12-03 | 2023-02-28 | Fmc Corporation | Pyrrolidinones herbicides |
| EP3230264B1 (en) | 2014-12-08 | 2019-09-11 | FMC Corporation | 3-oxo-3-(arylamino)propanoates, a process for their preparation, and their use in preparing pyrrolidinones |
| EP3280709B1 (en) | 2015-04-10 | 2021-05-26 | FMC Corporation | Substituted cyclic amides as herbicides |
| CN107531658B (zh) | 2015-04-27 | 2021-07-27 | Fmc公司 | 作为除草剂的丁内酯 |
| PL3294743T3 (pl) | 2015-05-12 | 2020-03-31 | Fmc Corporation | Podstawione arylem związki bicykliczne jako środki chwastobójcze |
| EP3303287B1 (en) | 2015-05-29 | 2020-12-16 | FMC Corporation | Substituted cyclic amides as herbicides |
| US10654804B2 (en) | 2015-06-02 | 2020-05-19 | Fmc Corporation | Substituted cyclic amides and their use as herbicides |
| AU2016303209B2 (en) | 2015-07-31 | 2021-04-01 | Fmc Corporation | Cyclic N-carboxamide compounds useful as herbicides |
| JP2020015664A (ja) * | 2016-11-21 | 2020-01-30 | 宇部興産株式会社 | 含窒素多環式ヘテロ環誘導体 |
| EP3558962B1 (en) | 2016-12-21 | 2023-07-12 | FMC Corporation | Nitrone herbicides |
| BR112019019551A2 (pt) | 2017-03-21 | 2020-04-22 | Fmc Corp | mistura, e, método para controlar o crescimento de vegetação indesejada |
| SG11201908640TA (en) | 2017-03-21 | 2019-10-30 | Fmc Corp | Pyrrolidinones and a process to prepare them |
| WO2018177837A1 (de) | 2017-03-30 | 2018-10-04 | Bayer Aktiengesellschaft | 4-cyclopentyl- und 4-cyclopropyl-2-oxopyrrolidin-3-carboxami d-derivate und verwandte verbindungen als herbizide pflanzenschutzmittel |
| WO2018177836A1 (de) | 2017-03-30 | 2018-10-04 | Bayer Aktiengesellschaft | N-cyclopropyl-2-oxopyrrolidin-3-carboxamid-derivate und verwandte verbindungen als herbizide pflanzenschutzmittel |
| AR111967A1 (es) | 2017-05-30 | 2019-09-04 | Fmc Corp | Amidas herbicidas |
| AR111839A1 (es) | 2017-05-30 | 2019-08-21 | Fmc Corp | Lactamas 3-sustituidas herbicidas |
| WO2019025156A1 (de) | 2017-08-03 | 2019-02-07 | Bayer Aktiengesellschaft | Substituierte pyrrolidinone sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| WO2020064260A1 (de) | 2018-09-24 | 2020-04-02 | Bayer Aktiengesellschaft | Substituierte 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamide sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| JP2022106302A (ja) * | 2019-05-30 | 2022-07-20 | 石原産業株式会社 | 除草組成物 |
| CN112844856B (zh) * | 2020-12-21 | 2021-11-26 | 中南大学 | 一种萤石和脉石浮选分离的复合抑制剂、复合浮选药剂和方法 |
| IL313538A (en) | 2021-12-15 | 2024-08-01 | Adama Agan Ltd | Useful compounds for the preparation of various agrochemicals and their markers |
| KR20250160506A (ko) * | 2023-03-23 | 2025-11-13 | 에프엠씨 코포레이션 | 제초제로서의 치환된 옥사졸리디논 및 이미다졸리논 |
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| AU2016259529A1 (en) | 2017-10-12 |
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| CN113402394B (zh) | 2024-04-26 |
| AR120921A2 (es) | 2022-03-30 |
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| BR112017021859B1 (pt) | 2022-05-10 |
| RU2017134776A (ru) | 2019-04-09 |
| US11634421B2 (en) | 2023-04-25 |
| US20200031836A1 (en) | 2020-01-30 |
| CN107592862A (zh) | 2018-01-16 |
| JP2018518470A (ja) | 2018-07-12 |
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