WO2024104954A1 - Cycloalkyloxyphényluraciles substitues et leurs sels, et leur utilisation comme principes actifs herbicides - Google Patents
Cycloalkyloxyphényluraciles substitues et leurs sels, et leur utilisation comme principes actifs herbicides Download PDFInfo
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- WO2024104954A1 WO2024104954A1 PCT/EP2023/081600 EP2023081600W WO2024104954A1 WO 2024104954 A1 WO2024104954 A1 WO 2024104954A1 EP 2023081600 W EP2023081600 W EP 2023081600W WO 2024104954 A1 WO2024104954 A1 WO 2024104954A1
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- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- aryl
- alkoxy
- methyl
- amino
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 65
- 230000002363 herbicidal effect Effects 0.000 title claims description 31
- 239000013543 active substance Substances 0.000 title claims description 16
- 239000004009 herbicide Substances 0.000 claims abstract description 37
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 9
- -1 tetramethyl-1,3,2-dioxaborolan-2-yl Chemical group 0.000 claims description 475
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 317
- 150000001875 compounds Chemical class 0.000 claims description 217
- 239000001257 hydrogen Substances 0.000 claims description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 56
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 51
- 150000002367 halogens Chemical class 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 36
- 239000011737 fluorine Substances 0.000 claims description 35
- 150000003254 radicals Chemical group 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 239000000460 chlorine Substances 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 24
- 238000009472 formulation Methods 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 21
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 20
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 18
- 125000002950 monocyclic group Chemical group 0.000 claims description 18
- 239000002689 soil Substances 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 230000008635 plant growth Effects 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 13
- 230000001276 controlling effect Effects 0.000 claims description 13
- 230000001105 regulatory effect Effects 0.000 claims description 13
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims description 12
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 12
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 11
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 10
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 5
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003337 fertilizer Substances 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- LQAOINCGMDEPDQ-UHFFFAOYSA-N 3-ethylpenta-1,2-diene Chemical group CCC(CC)=C=C LQAOINCGMDEPDQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
- 239000003630 growth substance Substances 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 239000000642 acaricide Substances 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 239000005645 nematicide Substances 0.000 claims description 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
- PAKGDPSCXSUALC-UHFFFAOYSA-N 3-methylbuta-1,2-diene Chemical group CC(C)=C=C PAKGDPSCXSUALC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 241000196324 Embryophyta Species 0.000 abstract description 118
- 230000012010 growth Effects 0.000 abstract description 10
- 241000209504 Poaceae Species 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 230000000694 effects Effects 0.000 description 63
- 239000004480 active ingredient Substances 0.000 description 38
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 28
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 22
- 239000002253 acid Substances 0.000 description 22
- 125000003342 alkenyl group Chemical group 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 230000009261 transgenic effect Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 17
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 240000007594 Oryza sativa Species 0.000 description 13
- 235000007164 Oryza sativa Nutrition 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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 12
- 239000012230 colorless oil Substances 0.000 description 12
- 125000004430 oxygen atom Chemical group O* 0.000 description 12
- 239000003880 polar aprotic solvent Substances 0.000 description 12
- 235000009566 rice Nutrition 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 244000062793 Sorghum vulgare Species 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 240000008042 Zea mays Species 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 244000038559 crop plants Species 0.000 description 10
- 239000008187 granular material Substances 0.000 description 10
- 125000001188 haloalkyl group Chemical group 0.000 description 10
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
- 235000019713 millet Nutrition 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
- 229910000024 caesium carbonate Inorganic materials 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 125000003636 chemical group Chemical group 0.000 description 8
- 239000004495 emulsifiable concentrate Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 239000000575 pesticide Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 125000002837 carbocyclic group Chemical group 0.000 description 7
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 229960003975 potassium Drugs 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000005504 Dicamba Substances 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 241000209219 Hordeum Species 0.000 description 6
- 239000005595 Picloram Substances 0.000 description 6
- 241000209056 Secale Species 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
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000004562 water dispersible granule Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical group C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 5
- 241000209761 Avena Species 0.000 description 5
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 235000007238 Secale cereale Nutrition 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical compound CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 238000010353 genetic engineering Methods 0.000 description 5
- 125000004438 haloalkoxy group Chemical group 0.000 description 5
- 125000004995 haloalkylthio group Chemical group 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 125000004043 oxo group Chemical group O=* 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 108010000700 Acetolactate synthase Proteins 0.000 description 4
- 240000002791 Brassica napus Species 0.000 description 4
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 241000219146 Gossypium Species 0.000 description 4
- 239000007821 HATU Substances 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- LKAHTZMLAOKUJF-UHFFFAOYSA-N ketospiradox-potassium Chemical compound [K+].CC=1C(C2(OCCO2)CCS2(=O)=O)=C2C(C)=CC=1C(=O)[C-]1C(=O)CCCC1=O LKAHTZMLAOKUJF-UHFFFAOYSA-N 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
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- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
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- 125000005647 linker group Chemical group 0.000 description 1
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- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- WMMYHMKUTCMAIJ-UHFFFAOYSA-M lithium;4-cyano-2,6-diiodophenolate Chemical compound [Li+].[O-]C1=C(I)C=C(C#N)C=C1I WMMYHMKUTCMAIJ-UHFFFAOYSA-M 0.000 description 1
- VIMSQXDDXJYTLW-UHFFFAOYSA-M lithium;5-bromo-3-butan-2-yl-6-methylpyrimidin-1-ide-2,4-dione Chemical compound [Li+].CCC(C)N1C(=O)[N-]C(C)=C(Br)C1=O VIMSQXDDXJYTLW-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- YMNRJYYHNXITFZ-UHFFFAOYSA-L magnesium;2,2,2-trichloroacetate Chemical compound [Mg+2].[O-]C(=O)C(Cl)(Cl)Cl.[O-]C(=O)C(Cl)(Cl)Cl YMNRJYYHNXITFZ-UHFFFAOYSA-L 0.000 description 1
- QPPXJFBMSFYKMM-UHFFFAOYSA-L magnesium;2,2-dichloropropanoate Chemical compound [Mg+2].CC(Cl)(Cl)C([O-])=O.CC(Cl)(Cl)C([O-])=O QPPXJFBMSFYKMM-UHFFFAOYSA-L 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 description 1
- RBNIGDFIUWJJEV-LLVKDONJSA-N methyl (2r)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-LLVKDONJSA-N 0.000 description 1
- AIBVECHZVPKHDS-GHYOLMRSSA-N methyl (2z,4e)-5-(6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoate Chemical compound COC(=O)\C=C(\C)/C=C/C1(O)C(C)=CC(=O)CC1(C)C#C AIBVECHZVPKHDS-GHYOLMRSSA-N 0.000 description 1
- YGWINKVROAENAL-UHFFFAOYSA-N methyl 1-bromocyclopentane-1-carboxylate Chemical compound COC(=O)C1(Br)CCCC1 YGWINKVROAENAL-UHFFFAOYSA-N 0.000 description 1
- SCHCPDWDIOTCMJ-UHFFFAOYSA-N methyl 2-(2,4-dichlorophenoxy)propanoate Chemical group COC(=O)C(C)OC1=CC=C(Cl)C=C1Cl SCHCPDWDIOTCMJ-UHFFFAOYSA-N 0.000 description 1
- YWGAULPFWIQKRB-UHFFFAOYSA-N methyl 2-(4-chloro-2-methylphenoxy)propanoate Chemical group COC(=O)C(C)OC1=CC=C(Cl)C=C1C YWGAULPFWIQKRB-UHFFFAOYSA-N 0.000 description 1
- PMJRLYSMEOLBIU-UHFFFAOYSA-N methyl 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)quinoline-3-carboxylate Chemical group COC(=O)C1=CC2=CC=CC=C2N=C1C1=NC(C)(C(C)C)C(=O)N1 PMJRLYSMEOLBIU-UHFFFAOYSA-N 0.000 description 1
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- NDQZMBNEHYSVPL-UHFFFAOYSA-N methyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OC)=CC=C(Cl)C2=C1 NDQZMBNEHYSVPL-UHFFFAOYSA-N 0.000 description 1
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 description 1
- BOIUPYHMTRFIJN-UHFFFAOYSA-N methyl 2-[(3-oxo-1h-isothiochromen-4-ylidene)methoxy]acetate Chemical compound C1=CC=C2C(=COCC(=O)OC)C(=O)SCC2=C1 BOIUPYHMTRFIJN-UHFFFAOYSA-N 0.000 description 1
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 description 1
- DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical group COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 description 1
- OUGVRUOROTYZSS-UHFFFAOYSA-N methyl 2-[(4-methoxy-6-methylsulfanylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(SC)=N1 OUGVRUOROTYZSS-UHFFFAOYSA-N 0.000 description 1
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 description 1
- VGBNSONMEGTIDX-UHFFFAOYSA-N methyl 2-[(4-methylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC=CC(C)=N1 VGBNSONMEGTIDX-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- IAUMNRCGDHLAMJ-UHFFFAOYSA-N methyl 2-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 IAUMNRCGDHLAMJ-UHFFFAOYSA-N 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
- HQTUEAOWLVWJLF-UHFFFAOYSA-N methyl 3,6-dichloropyridine-2-carboxylate Chemical group COC(=O)C1=NC(Cl)=CC=C1Cl HQTUEAOWLVWJLF-UHFFFAOYSA-N 0.000 description 1
- QPTPZPIXUPELRM-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]sulfanylpropanoylamino]propanoate Chemical compound C1=C(Cl)C(SC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F QPTPZPIXUPELRM-UHFFFAOYSA-N 0.000 description 1
- MABPXDINJLMBST-UHFFFAOYSA-N methyl 3-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]-5-methyl-4H-1,2-oxazole-5-carboxylate Chemical compound ClC1=C(C=C(C(=C1)F)N1C(N(C(=CC1=O)C(F)(F)F)C)=O)C1=NOC(C1)(C(=O)OC)C MABPXDINJLMBST-UHFFFAOYSA-N 0.000 description 1
- FWDQLSHRVKQKBS-UHFFFAOYSA-N methyl 4-(4-chloro-2-methylphenoxy)butanoate Chemical group COC(=O)CCCOC1=CC=C(Cl)C=C1C FWDQLSHRVKQKBS-UHFFFAOYSA-N 0.000 description 1
- RTAXDHMFSZODHZ-UHFFFAOYSA-N methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1h-indol-6-yl)pyridine-2-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C3NC=CC3=CC=2)F)=C1F RTAXDHMFSZODHZ-UHFFFAOYSA-N 0.000 description 1
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 description 1
- WXUNXXKSYBUHMK-UHFFFAOYSA-N methyl 4-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate;methyl 5-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical compound COC(=O)C1=CC=C(C)C=C1C1=NC(C)(C(C)C)C(=O)N1.COC(=O)C1=CC(C)=CC=C1C1=NC(C)(C(C)C)C(=O)N1 WXUNXXKSYBUHMK-UHFFFAOYSA-N 0.000 description 1
- AHGMXAFUHVRQAD-UHFFFAOYSA-N methyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 AHGMXAFUHVRQAD-UHFFFAOYSA-N 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229960002939 metizoline Drugs 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-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
- 230000005855 radiation Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- SLUXPOIDTZWGCG-UHFFFAOYSA-N rhizobitoxine Natural products OCC(N)COC=CC(N)C(O)=O SLUXPOIDTZWGCG-UHFFFAOYSA-N 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- RTWIRLHWLMNVCC-WQYNNSOESA-M sodium (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]propanoate Chemical compound [Na+].[O-]C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O RTWIRLHWLMNVCC-WQYNNSOESA-M 0.000 description 1
- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 1
- SGUSXTMVKMPQKI-UHFFFAOYSA-M sodium;2,2,3,3-tetrafluoropropanoate Chemical compound [Na+].[O-]C(=O)C(F)(F)C(F)F SGUSXTMVKMPQKI-UHFFFAOYSA-M 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-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
- DHJHUXNTNSRSEX-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)propanoate Chemical compound [Na+].[O-]C(=O)C(C)OC1=CC=C(Cl)C=C1C DHJHUXNTNSRSEX-UHFFFAOYSA-M 0.000 description 1
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 description 1
- JUNDBKFAZXZKRA-MAFYXNADSA-M sodium;2-[(e)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylate Chemical compound [Na+].N=1C=CC=C(C([O-])=O)C=1C(/C)=N/NC(=O)NC1=CC(F)=CC(F)=C1 JUNDBKFAZXZKRA-MAFYXNADSA-M 0.000 description 1
- JQYJSVBNPUHHKB-UHFFFAOYSA-M sodium;2-methyl-4,6-dinitrophenolate Chemical compound [Na+].CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1[O-] JQYJSVBNPUHHKB-UHFFFAOYSA-M 0.000 description 1
- ZIJQUHYXJXYXBC-UHFFFAOYSA-M sodium;3-(cyclopropen-1-yl)propanoate Chemical compound [Na+].[O-]C(=O)CCC1=CC1 ZIJQUHYXJXYXBC-UHFFFAOYSA-M 0.000 description 1
- WMWBBXKLYSGKDY-UHFFFAOYSA-M sodium;3-amino-2,5-dichlorobenzoate Chemical compound [Na+].NC1=CC(Cl)=CC(C([O-])=O)=C1Cl WMWBBXKLYSGKDY-UHFFFAOYSA-M 0.000 description 1
- KBRBTPNRBSCEJD-UHFFFAOYSA-M sodium;3-cycloprop-2-en-1-ylpropanoate Chemical compound [Na+].[O-]C(=O)CCC1C=C1 KBRBTPNRBSCEJD-UHFFFAOYSA-M 0.000 description 1
- PPKIJAQKBAYNNL-UHFFFAOYSA-M sodium;4-(2,4-dichlorophenoxy)butanoate Chemical compound [Na+].[O-]C(=O)CCCOC1=CC=C(Cl)C=C1Cl PPKIJAQKBAYNNL-UHFFFAOYSA-M 0.000 description 1
- GABUSZPTCJGKGB-UHFFFAOYSA-M sodium;4-(4-chloro-2-methylphenoxy)butanoate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O GABUSZPTCJGKGB-UHFFFAOYSA-M 0.000 description 1
- JXIAOZNHSODSNJ-UHFFFAOYSA-M sodium;5-bromo-3-butan-2-yl-6-methylpyrimidin-1-ide-2,4-dione Chemical compound [Na+].CCC(C)N1C(=O)[N-]C(C)=C(Br)C1=O JXIAOZNHSODSNJ-UHFFFAOYSA-M 0.000 description 1
- YPMAQKXGDCKXPE-WCCKRBBISA-M sodium;[(3s)-3-amino-3-carboxypropyl]-methylphosphinate Chemical compound [Na+].CP([O-])(=O)CC[C@H](N)C(O)=O YPMAQKXGDCKXPE-WCCKRBBISA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 229940063675 spermine Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl 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
- 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 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- 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
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- QQDYOLJZDUADHV-CJNGLKHVSA-N tetflupyrolimet Chemical compound FC1=C(C=CC=C1)NC(=O)[C@H]1C(N(C[C@@H]1C1=CC(=CC=C1)C(F)(F)F)C)=O QQDYOLJZDUADHV-CJNGLKHVSA-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
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003777 thiepinyl group Chemical group 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 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
- 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
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 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
- 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
- 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
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention concerne des cycloalkyloxyphényluraciles substitués de formule générale (I) ou des sels de ceux-ci, les radicaux dans la formule générale (I) correspondant aux définitions données dans la description, et leur utilisation en tant qu'herbicides, en particulier pour lutter contre les adventices et/ou les mauvaises herbes dans les cultures, et/ou en tant que régulateurs de croissance des plantes pour influencer la croissance des cultures.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP22207817 | 2022-11-16 | ||
| EP22207817.2 | 2022-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2024104954A1 true WO2024104954A1 (fr) | 2024-05-23 |
Family
ID=84358856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2023/081600 WO2024104954A1 (fr) | 2022-11-16 | 2023-11-13 | Cycloalkyloxyphényluraciles substitues et leurs sels, et leur utilisation comme principes actifs herbicides |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2024104954A1 (fr) |
Citations (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2906507A1 (de) | 1979-02-20 | 1980-08-28 | Bayer Ag | Mittel zur regulierung des pflanzenwachstums |
| EP0030287A1 (fr) | 1979-11-29 | 1981-06-17 | Bayer Ag | Dérivés de l'acide amino-1 cyclopropanecarboxylique, procédés pour leur préparation, leur utilisation comme régulateurs de la croissance de végétaux et compositions contenant de tels dérivés |
| EP0086750A2 (fr) | 1982-02-17 | 1983-08-24 | Ciba-Geigy Ag | Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables |
| EP0094349A2 (fr) | 1982-05-07 | 1983-11-16 | Ciba-Geigy Ag | Utilisation de dérivés de quinoléine pour protéger des plantes cultivées |
| DE3335514A1 (de) | 1983-09-30 | 1985-04-18 | Bayer Ag, 5090 Leverkusen | 1-methylamino-cyclopropan-1-carbonsaeure-derivate |
| JPS6087254A (ja) | 1983-10-19 | 1985-05-16 | Japan Carlit Co Ltd:The | 新規尿素化合物及びそれを含有する除草剤 |
| EP0174562A2 (fr) | 1984-09-11 | 1986-03-19 | Hoechst Aktiengesellschaft | Agents pour la protection de plantes basés sur des dérivés de 1,2,4- briazole ainsi que dérivés 1,2,4-triazole |
| EP0191736A2 (fr) | 1985-02-14 | 1986-08-20 | Ciba-Geigy Ag | Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables |
| EP0255047A1 (fr) | 1986-07-31 | 1988-02-03 | Ciba-Geigy Ag | Aryl-3 uraciles et leur application comme herbicides |
| EP0268554A2 (fr) | 1986-10-22 | 1988-05-25 | Ciba-Geigy Ag | Dérivés d'acide diphényl-1,5-pyrazol-3-carbonique pour la protection de plantes de culture |
| EP0269806A1 (fr) | 1986-10-04 | 1988-06-08 | Hoechst Aktiengesellschaft | Dérivés d'acide phénylpyrazolcarbonique, leur préparation et leur utilisation comme agents régulateurs de croissance des plantes et antidote |
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| EP0492366A2 (fr) | 1990-12-21 | 1992-07-01 | Hoechst Schering AgrEvo GmbH | Nouveaux dérivés de chloro-5-quinoline-8-acide oxyalkanecarboniques, procédé pour leur préparation et leur utilisation comme antidote d'herbicides |
| EP0582198A2 (fr) | 1992-08-01 | 1994-02-09 | Hoechst Schering AgrEvo GmbH | Composés (hétéro-)aryliques substitués, procédé pour leur préparation, compositions les contenant et leur utilisation comme agents de protection |
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| JP2001172265A (ja) | 1999-12-15 | 2001-06-26 | Sumitomo Chem Co Ltd | ヒドロキサム酸誘導体およびその用途 |
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| WO2004084631A1 (fr) | 2003-03-26 | 2004-10-07 | Bayer Cropscience Gmbh | Utilisation de composés aromatiques hydroxy comme phytoprotecteurs |
| WO2005015994A1 (fr) | 2003-08-05 | 2005-02-24 | Bayer Cropscience Gmbh | Utilisation d'aromates hydroxy comme phytoprotecteurs |
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| WO2007023764A1 (fr) | 2005-08-26 | 2007-03-01 | Kumiai Chemical Industry Co., Ltd. | Agent servant à réduire les effets nocifs d’un herbicide et composition d’herbicide ayant des effets nocifs réduits |
| WO2008131860A2 (fr) | 2007-04-30 | 2008-11-06 | Bayer Cropscience Ag | Pyridone-carboxamides, phytoprotecteurs contenant ces composés, procédés pour leur production et leur utilisation |
| WO2008131861A1 (fr) | 2007-04-30 | 2008-11-06 | Bayer Cropscience Ag | Utilisation de pyridin-2-oxy-3-carbonamides comme phytoprotecteurs |
| WO2010038953A2 (fr) | 2008-10-02 | 2010-04-08 | 한국화학연구원 | Composés à base d’uracile, et herbicides en comportant |
| EP2248421A1 (fr) | 2009-05-07 | 2010-11-10 | GMI - Gregor-Mendel-Institut für Molekulare Pflanzenbiologie GmbH | Accumulation de biomasse dans les plantes |
| KR20110110420A (ko) | 2010-04-01 | 2011-10-07 | 한국화학연구원 | 제초성 우라실계 화합물 및 이를 포함하는 제초제 |
| WO2020013500A1 (fr) | 2018-07-10 | 2020-01-16 | 주식회사 경농 | Composé à base d'uracile et composition herbicide le comprenant |
| WO2021105101A1 (fr) | 2019-11-26 | 2021-06-03 | Bayer Aktiengesellschaft | Dérivés d'acide acétique [(1,5-diphényl-1h-1,2,4-triazol-3-yl)oxy] et sels de ceux-ci, compositions de protection des cultures les comprenant, leurs procédés de production et utilisation de ceux-ci en tant que phytoprotecteurs |
| WO2021259224A1 (fr) | 2020-06-23 | 2021-12-30 | 沈阳中化农药化工研发有限公司 | Composé triazine benzoate et son application |
-
2023
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