HRP20050074A2 - 4-trifluoromethylpyrazolyl substituted pyridines and pyrimidines - Google Patents

Info

Publication number

HRP20050074A2

HRP20050074A2 HR20050074A HRP20050074A HRP20050074A2 HR P20050074 A2 HRP20050074 A2 HR P20050074A2 HR 20050074 A HR20050074 A HR 20050074A HR P20050074 A HRP20050074 A HR P20050074A HR P20050074 A2 HRP20050074 A2 HR P20050074A2

Authority

HR

Croatia

Prior art keywords

halogen

alkyl

alkoxy

hydrogen

compounds

Prior art date

2002-07-25

Links

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• -1 4-trifluoromethylpyrazolyl Chemical group 0.000 title claims abstract description 17
• 150000003222 pyridines Chemical class 0.000 title abstract description 6
• 150000003230 pyrimidines Chemical class 0.000 title abstract description 6
• 239000004009 herbicide Substances 0.000 claims abstract description 18
• 150000001875 compounds Chemical class 0.000 claims description 79
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
• 239000000203 mixture Substances 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 150000002367 halogens Chemical class 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 150000002431 hydrogen Chemical class 0.000 claims description 19
• 238000009472 formulation Methods 0.000 claims description 18
• 238000000034 method Methods 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
• 230000002363 herbicidal effect Effects 0.000 claims description 12
• 230000012010 growth Effects 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 4
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 4
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
• 150000001204 N-oxides Chemical class 0.000 claims description 4
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 229920002554 vinyl polymer Polymers 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims description 2
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000006646 halo(C3- C5)cycloalkyl group Chemical group 0.000 claims description 2
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
• 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 2
• 244000045561 useful plants Species 0.000 claims 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
• 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
• 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
• 125000003118 aryl group Chemical group 0.000 abstract description 3
• 229910052799 carbon Inorganic materials 0.000 abstract description 2
• 241000196324 Embryophyta Species 0.000 description 68
• 239000013543 active substance Substances 0.000 description 27
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• 125000001424 substituent group Chemical group 0.000 description 17
• 150000002148 esters Chemical class 0.000 description 16
• 239000008187 granular material Substances 0.000 description 16
• 239000000839 emulsion Substances 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
• 239000012141 concentrate Substances 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 11
• 239000007921 spray Substances 0.000 description 11
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 108090000623 proteins and genes Proteins 0.000 description 10
• 239000002253 acid Substances 0.000 description 9
• 244000038559 crop plants Species 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 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 8
• 240000007594 Oryza sativa Species 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• 235000007164 Oryza sativa Nutrition 0.000 description 7
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
• 235000002639 sodium chloride Nutrition 0.000 description 7
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 239000003995 emulsifying agent Substances 0.000 description 6
• 235000019439 ethyl acetate Nutrition 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 238000002156 mixing Methods 0.000 description 6
• 239000002689 soil Substances 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• 238000005160 1H NMR spectroscopy Methods 0.000 description 5
• 244000237956 Amaranthus retroflexus Species 0.000 description 5
• 235000013479 Amaranthus retroflexus Nutrition 0.000 description 5
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 5
• 235000010469 Glycine max Nutrition 0.000 description 5
• 240000003461 Setaria viridis Species 0.000 description 5
• 235000002248 Setaria viridis Nutrition 0.000 description 5
• 240000008042 Zea mays Species 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 238000004519 manufacturing process Methods 0.000 description 5
• 239000010695 polyglycol Substances 0.000 description 5
• 229920000151 polyglycol Polymers 0.000 description 5
• 235000009566 rice Nutrition 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 241000894007 species Species 0.000 description 5
• KDEJQUNODYXYBJ-UHFFFAOYSA-N 4-(trifluoromethyl)-1h-pyrazole Chemical compound FC(F)(F)C=1C=NNC=1 KDEJQUNODYXYBJ-UHFFFAOYSA-N 0.000 description 4
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
• 125000000217 alkyl group Chemical group 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• 238000011097 chromatography purification Methods 0.000 description 4
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
• 239000003921 oil Substances 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• 238000005507 spraying Methods 0.000 description 4
• 239000004094 surface-active agent Substances 0.000 description 4
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• 239000005995 Aluminium silicate Substances 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• 108091026890 Coding region Proteins 0.000 description 3
• 229920000742 Cotton Polymers 0.000 description 3
• 108020004414 DNA Proteins 0.000 description 3
• 241000192043 Echinochloa Species 0.000 description 3
• 244000068988 Glycine max Species 0.000 description 3
• 239000005562 Glyphosate Substances 0.000 description 3
• 244000299507 Gossypium hirsutum Species 0.000 description 3
• 240000005979 Hordeum vulgare Species 0.000 description 3
• 235000007340 Hordeum vulgare Nutrition 0.000 description 3
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
• 108091028043 Nucleic acid sequence Proteins 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 239000004372 Polyvinyl alcohol Substances 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• 229920002472 Starch Polymers 0.000 description 3
• 240000006694 Stellaria media Species 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 235000021307 Triticum Nutrition 0.000 description 3
• 244000098338 Triticum aestivum Species 0.000 description 3
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
• 235000012211 aluminium silicate Nutrition 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
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• 239000000084 colloidal system Substances 0.000 description 3
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• 150000004665 fatty acids Chemical group 0.000 description 3
• 150000002191 fatty alcohols Chemical class 0.000 description 3
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• FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 3
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• 235000019341 magnesium sulphate Nutrition 0.000 description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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• 229910000027 potassium carbonate Inorganic materials 0.000 description 3
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• OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 3
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• RETNEVJQGWGCGZ-UHFFFAOYSA-N 2-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-6-[4-(trifluoromethyl)pyrazol-1-yl]pyridine Chemical compound CN1N=C(C(F)(F)F)C=C1OC1=CC=CC(N2N=CC(=C2)C(F)(F)F)=N1 RETNEVJQGWGCGZ-UHFFFAOYSA-N 0.000 description 2
• IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 2
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• ZJCJWGRLDSFQOL-UHFFFAOYSA-N 4-methoxy-2-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-6-[4-(trifluoromethyl)pyrazol-1-yl]pyridine Chemical compound N=1C(N2N=CC(=C2)C(F)(F)F)=CC(OC)=CC=1OC1=CC(C(F)(F)F)=NN1C ZJCJWGRLDSFQOL-UHFFFAOYSA-N 0.000 description 2
• ODXONCFDHQXCJO-UHFFFAOYSA-N 4-methyl-2-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxy-6-[4-(trifluoromethyl)pyrazol-1-yl]pyridine Chemical compound N=1C(N2N=CC(=C2)C(F)(F)F)=CC(C)=CC=1OC1=CC(C(F)(F)F)=NN1C ODXONCFDHQXCJO-UHFFFAOYSA-N 0.000 description 2
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• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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• WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical class O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 2
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