SK159697A3 - Herbicidal substituted 3-aryl-pyrazoles - Google Patents
Herbicidal substituted 3-aryl-pyrazoles Download PDFInfo
- Publication number
- SK159697A3 SK159697A3 SK1596-97A SK159697A SK159697A3 SK 159697 A3 SK159697 A3 SK 159697A3 SK 159697 A SK159697 A SK 159697A SK 159697 A3 SK159697 A3 SK 159697A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- alkyl
- compounds
- halogen
- substituted
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 29
- -1 cyano, hydroxy Chemical group 0.000 claims abstract description 113
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 238000000034 method Methods 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
- 150000002367 halogens Chemical class 0.000 claims abstract description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 13
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 150000004677 hydrates Chemical class 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000012039 electrophile Substances 0.000 claims description 5
- 229910052739 hydrogen Chemical group 0.000 claims description 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000007818 Grignard reagent Substances 0.000 claims description 3
- 150000003973 alkyl amines Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000001721 carbon Chemical class 0.000 claims description 3
- 125000005265 dialkylamine group Chemical group 0.000 claims description 3
- 150000004795 grignard reagents Chemical class 0.000 claims description 3
- WAYPDRMFHYYNQN-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)pyrazol-3-yl]-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)C)=C1F WAYPDRMFHYYNQN-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- IDJSXCZIIOBGTL-UHFFFAOYSA-N ethyl 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)pyrazol-3-yl]-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)C)=C1F IDJSXCZIIOBGTL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- BHCMKYAHWGAKMU-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[4-(difluoromethyl)-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)C(F)F)=C1F BHCMKYAHWGAKMU-UHFFFAOYSA-N 0.000 claims description 2
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 150000002429 hydrazines Chemical class 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 85
- 238000012360 testing method Methods 0.000 description 58
- 230000005764 inhibitory process Effects 0.000 description 54
- 239000000243 solution Substances 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 239000007787 solid Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000945 filler Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 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
- 239000004009 herbicide Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000010561 standard procedure Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000012025 fluorinating agent Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000001850 reproductive effect Effects 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- YTGFHAACURJTPL-UHFFFAOYSA-N 1-chloro-4-(1,1-diethoxypropyl)benzene Chemical compound CCOC(CC)(OCC)C1=CC=C(Cl)C=C1 YTGFHAACURJTPL-UHFFFAOYSA-N 0.000 description 3
- JYEFCZBWOTZDOL-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[4-formyl-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]benzoic acid Chemical compound O=CC1=C(C(F)(F)F)N(C)N=C1C1=CC(C(O)=O)=C(Cl)C=C1F JYEFCZBWOTZDOL-UHFFFAOYSA-N 0.000 description 3
- UCRBUQZLSCZSIH-UHFFFAOYSA-N 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)pyrazol-3-yl]-4-fluorobenzoic acid Chemical compound CN1C(C(F)(F)F)=C(C)C(C=2C(=CC(Cl)=C(C(O)=O)C=2)F)=N1 UCRBUQZLSCZSIH-UHFFFAOYSA-N 0.000 description 3
- XMSPILXFAZRRNT-UHFFFAOYSA-N 3-(4-chlorophenyl)-1,4-dimethyl-5-(trifluoromethyl)pyrazole Chemical compound CN1C(C(F)(F)F)=C(C)C(C=2C=CC(Cl)=CC=2)=N1 XMSPILXFAZRRNT-UHFFFAOYSA-N 0.000 description 3
- HQWNZBWPMHKKCW-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-methyl-5-(trifluoromethyl)-1h-pyrazole Chemical compound N1N=C(C(F)(F)F)C(C)=C1C1=CC=C(Cl)C=C1 HQWNZBWPMHKKCW-UHFFFAOYSA-N 0.000 description 3
- XQNCVNXVIFYARG-UHFFFAOYSA-N 3-[5-(bromomethyl)-4-chloro-2-fluorophenyl]-1,4-dimethyl-5-(trifluoromethyl)pyrazole Chemical compound CN1C(C(F)(F)F)=C(C)C(C=2C(=CC(Cl)=C(CBr)C=2)F)=N1 XQNCVNXVIFYARG-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229940100389 Sulfonylurea Drugs 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- XUCIDZVUYQIGRZ-UHFFFAOYSA-N [2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)pyrazol-3-yl]-4-fluorophenyl]methanol Chemical compound CN1C(C(F)(F)F)=C(C)C(C=2C(=CC(Cl)=C(CO)C=2)F)=N1 XUCIDZVUYQIGRZ-UHFFFAOYSA-N 0.000 description 3
- 150000003869 acetamides Chemical class 0.000 description 3
- 150000008061 acetanilides Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000011097 chromatography purification Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
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- 210000003608 fece Anatomy 0.000 description 3
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- 230000002140 halogenating effect Effects 0.000 description 3
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- 239000010871 livestock manure Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NOINPQZPPCTQRA-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-[4-formyl-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)C=O)=C1F NOINPQZPPCTQRA-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- RLMWUKCOJRSAAC-UHFFFAOYSA-N 3-(2,5-difluorophenyl)-1,4-dimethyl-5-(trifluoromethyl)pyrazole Chemical compound CN1C(C(F)(F)F)=C(C)C(C=2C(=CC=C(F)C=2)F)=N1 RLMWUKCOJRSAAC-UHFFFAOYSA-N 0.000 description 2
- PHWMNCUTMAFAQX-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-ethoxy-1,1,1-trifluoro-3-methylbut-3-en-2-one Chemical compound FC(F)(F)C(=O)C(C)=C(OCC)C1=CC=C(Cl)C=C1 PHWMNCUTMAFAQX-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- YNMHKERYELPEEF-UHFFFAOYSA-N 4-bromo-3-(5'-carboxy-4'-chloro-2'-fluorophenyl)-1-methyl-5-trifluoromethyl-pyrazol Chemical compound BrC1=C(C(F)(F)F)N(C)N=C1C1=CC(C(O)=O)=C(Cl)C=C1F YNMHKERYELPEEF-UHFFFAOYSA-N 0.000 description 2
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical class N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 2
- 241000743985 Alopecurus Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 240000005702 Galium aparine Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 229910015275 MoF 6 Inorganic materials 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Chemical class 0.000 description 2
- 241000533293 Sesbania emerus Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000002594 Solanum nigrum Nutrition 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
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- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
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- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical class [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
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- 229910000103 lithium hydride Inorganic materials 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- DLCUBZPWWQNAAF-UHFFFAOYSA-N s-propyl n,n-di(propan-2-yl)carbamothioate Chemical compound CCCSC(=O)N(C(C)C)C(C)C DLCUBZPWWQNAAF-UHFFFAOYSA-N 0.000 description 1
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- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
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- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
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- 239000002426 superphosphate Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 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
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- MPSUGQWRVNRJEE-UHFFFAOYSA-N triazol-1-amine Chemical compound NN1C=CN=N1 MPSUGQWRVNRJEE-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- A01N43/56—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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/476,794 US5675017A (en) | 1995-06-07 | 1995-06-07 | Herbicidal substituted 3-aryl-pyrazoles |
| PCT/US1996/008648 WO1996040643A1 (en) | 1995-06-07 | 1996-06-03 | Herbicidal substituted 3-aryl-pyrazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK159697A3 true SK159697A3 (en) | 1998-09-09 |
Family
ID=23893274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1596-97A SK159697A3 (en) | 1995-06-07 | 1996-06-03 | Herbicidal substituted 3-aryl-pyrazoles |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5675017A (cs) |
| EP (1) | EP0846105A1 (cs) |
| JP (1) | JPH11506767A (cs) |
| AR (1) | AR005226A1 (cs) |
| AU (1) | AU713398B2 (cs) |
| CZ (1) | CZ384997A3 (cs) |
| HU (1) | HUP9900968A3 (cs) |
| PL (1) | PL323728A1 (cs) |
| SK (1) | SK159697A3 (cs) |
| WO (1) | WO1996040643A1 (cs) |
| ZA (1) | ZA964324B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3217191B2 (ja) * | 1992-07-16 | 2001-10-09 | ビーエーエスエフ アクチェンゲゼルシャフト | ヘテロ芳香族化合物およびこれを含有する植物保護剤 |
| JPH11515009A (ja) * | 1995-10-26 | 1999-12-21 | ビーエーエスエフ アクチェンゲゼルシャフト | 置換４，５−ジ（トリフルオロメチル）ピラゾール |
| PT1020448E (pt) * | 1996-03-21 | 2005-05-31 | Isagro Ricerca Srl | Aril-heterociclos com actividade herbicida |
| DE19615259A1 (de) * | 1996-04-18 | 1997-10-23 | Bayer Ag | 3-Cyanoaryl-pyrazole |
| WO1998005649A1 (de) | 1996-08-01 | 1998-02-12 | Basf Aktiengesellschaft | Substituierte 3-phenylpyrazole |
| UA53679C2 (uk) | 1996-12-16 | 2003-02-17 | Басф Акцієнгезелльшафт | Заміщені піразол-3-ілбензазоли, спосіб їх одержання (варіанти), гербіцидний засіб та спосіб його одержання, засіб для десикації і/або дефоліації рослин та спосіб його одержання, спосіб боротьби з небажаним ростом рослин та спосіб десикації і/або дефоліації рослин |
| AU6719498A (en) * | 1997-02-27 | 1998-09-18 | Basf Aktiengesellschaft | Substituted 3-phenyl pyrazoles |
| US6541273B1 (en) | 1999-11-12 | 2003-04-01 | Aventis Cropscience, S.A. | Multiple sorbent cartridges for solid phase extraction |
| EP1436285A4 (en) * | 2001-09-18 | 2004-12-15 | Onconova Therapeutics Inc | METHOD FOR PRODUCING 1,5-DIARYL-3-SUBSTITUTED PYRAZOLES |
| US7449481B2 (en) * | 2004-04-13 | 2008-11-11 | Cephalon, Inc. | Thio-substituted biaryl-methanesulfinyl derivatives |
| CN101941941B (zh) * | 2009-07-06 | 2012-09-12 | 中国中化股份有限公司 | 一种羧酸酯类化合物及其用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2784925B2 (ja) * | 1988-09-07 | 1998-08-13 | 日本農薬株式会社 | ３又は５−フェニルピラゾール類又はその塩及び除草剤 |
| JPH0393774A (ja) * | 1989-09-07 | 1991-04-18 | Nippon Nohyaku Co Ltd | ３又は５―フェニルピラゾール類又はその塩及び除草剤 |
| US5281571A (en) * | 1990-10-18 | 1994-01-25 | Monsanto Company | Herbicidal benzoxazinone- and benzothiazinone-substituted pyrazoles |
-
1995
- 1995-06-07 US US08/476,794 patent/US5675017A/en not_active Expired - Fee Related
-
1996
- 1996-05-28 ZA ZA964324A patent/ZA964324B/xx unknown
- 1996-06-03 AU AU59775/96A patent/AU713398B2/en not_active Ceased
- 1996-06-03 WO PCT/US1996/008648 patent/WO1996040643A1/en not_active Ceased
- 1996-06-03 EP EP96917097A patent/EP0846105A1/en not_active Withdrawn
- 1996-06-03 PL PL96323728A patent/PL323728A1/xx unknown
- 1996-06-03 HU HU9900968A patent/HUP9900968A3/hu unknown
- 1996-06-03 SK SK1596-97A patent/SK159697A3/sk unknown
- 1996-06-03 CZ CZ973849A patent/CZ384997A3/cs unknown
- 1996-06-03 JP JP9501176A patent/JPH11506767A/ja active Pending
- 1996-06-06 AR ARP960102990A patent/AR005226A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9900968A3 (en) | 2001-08-28 |
| ZA964324B (en) | 1996-12-06 |
| US5675017A (en) | 1997-10-07 |
| CZ384997A3 (cs) | 1998-07-15 |
| AU713398B2 (en) | 1999-12-02 |
| EP0846105A1 (en) | 1998-06-10 |
| PL323728A1 (en) | 1998-04-14 |
| AR005226A1 (es) | 1999-04-28 |
| HUP9900968A2 (hu) | 1999-07-28 |
| JPH11506767A (ja) | 1999-06-15 |
| AU5977596A (en) | 1996-12-30 |
| WO1996040643A1 (en) | 1996-12-19 |
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