CN1420873A - 取代的苯基尿嘧啶类 - Google Patents
取代的苯基尿嘧啶类 Download PDFInfo
- Publication number
- CN1420873A CN1420873A CN01807438A CN01807438A CN1420873A CN 1420873 A CN1420873 A CN 1420873A CN 01807438 A CN01807438 A CN 01807438A CN 01807438 A CN01807438 A CN 01807438A CN 1420873 A CN1420873 A CN 1420873A
- Authority
- CN
- China
- Prior art keywords
- cyano
- methyl
- general formula
- alkyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 claims abstract description 48
- -1 cyano- Chemical class 0.000 claims description 668
- 150000001875 compounds Chemical class 0.000 claims description 105
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000000460 chlorine Substances 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 150000001448 anilines Chemical class 0.000 claims description 10
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 125000004306 triazinyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005881 triazolinyl group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 3
- 150000004692 metal hydroxides Chemical class 0.000 claims description 3
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 2
- UIKIQOAXFYAWPW-UHFFFAOYSA-N 5-phenyl-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(=O)NC=C1C1=CC=CC=C1 UIKIQOAXFYAWPW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- CHKQALUEEULCPZ-UHFFFAOYSA-N amino 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S(=O)(=O)ON)C(C)=C1 CHKQALUEEULCPZ-UHFFFAOYSA-N 0.000 claims description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- YLACRFYIUQZNIV-UHFFFAOYSA-N o-(2,4-dinitrophenyl)hydroxylamine Chemical compound NOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YLACRFYIUQZNIV-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 238000007350 electrophilic reaction Methods 0.000 claims 1
- 238000007344 nucleophilic reaction Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 9
- 241000196324 Embryophyta Species 0.000 description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 24
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 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 9
- 239000002420 orchard Substances 0.000 description 9
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000005582 Metosulam Substances 0.000 description 6
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000219198 Brassica Species 0.000 description 3
- 235000011331 Brassica Nutrition 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 235000005775 Setaria Nutrition 0.000 description 3
- 241000232088 Setaria <nematode> Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000002634 Solanum Nutrition 0.000 description 3
- 241000207763 Solanum Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 235000016993 Agrimonia Nutrition 0.000 description 2
- 244000307697 Agrimonia eupatoria Species 0.000 description 2
- 101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 235000005206 Hibiscus Nutrition 0.000 description 2
- 235000007185 Hibiscus lunariifolius Nutrition 0.000 description 2
- 244000284380 Hibiscus rosa sinensis Species 0.000 description 2
- 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 2
- 240000007171 Imperata cylindrica Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000219053 Rumex Species 0.000 description 2
- 241000209051 Saccharum Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BWKDLDWUVLGWFC-UHFFFAOYSA-N calcium;azanide Chemical compound [NH2-].[NH2-].[Ca+2] BWKDLDWUVLGWFC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 235000004879 dioscorea Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 235000014134 echinacea Nutrition 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- TUDUDQJRUPFUMA-UHFFFAOYSA-M ethyl(trioctyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CC)(CCCCCCCC)CCCCCCCC TUDUDQJRUPFUMA-UHFFFAOYSA-M 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 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 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 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
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 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
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- SNNIPOQLGBPXPS-UHFFFAOYSA-M tetraoctylazanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC SNNIPOQLGBPXPS-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- 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
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
通式(I)的苯基尿嘧啶类,其中Q,R1,R2,R3,R4,R5和R6代表说明书中列举的定义。本发明还涉及它的制备方法和作为除草剂的用途。
Description
本发明涉及新的取代的苯基尿嘧啶类,它们的制备方法以及作为作物处理剂,特别是作为除草剂的用途。
已知某些取代的苯基尿嘧啶类具有除草活性(参见EP 408382/US5084084/US 5127935/US 5154755,EP 563384,EP 648749,US 4979982,US 5169430,WO91/00278,WO-A-97/01541,WO-A-00/02866,WO-A-98/41093)。然而,至今这些化合物还没有受到足够的重视。
因此,本发明提供了新的通式(I)取代的苯基尿嘧啶类
其中
Q代表O(氧),S(硫),SO或SO2,
R1代表氢,氨基,任选地被氰基-,卤素-或C1-C4-烷氧基-取代的带有1-4个原子的烷基或各自任选地被卤素取代的各自带有2-4个碳原子的键烯基或炔基,
R2代表氰基,羧基,氨基甲酰基,硫代氨基甲酰基或各自任选地被氰基-,卤素-或C1-C4-烷氧基-取代的各自带有1-4个碳原子的烷基或烷氧基羰基,
R3代表氢,卤素或任选地被卤素取代的带有1-4个碳原子的烷基,
R4代表氢,硝基,氰基或卤素,
R5代表氰基,硫代氨基甲酰基,溴或各自任选地被卤素取代的各自带有1-4个碳原子的烷基或烷氧基,以及
R6代表任选地被硝基-,羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,卤素-,C1-C4-烷基-,氰基-C1-C4-烷基-,羧基-C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-C1-C4-烷基-,C1-C4-烷氧基羰基-C1-C4-烷基-,C1-C4-烷基氨基羰基烷基-,二-(C1-C4-烷基)-氨基羰基烷基-,C1-C4-烷氧基-,氰基-C1-C4-烷氧基-,C1-C4-卤代烷氧基-,C1-C4-烷氧基-C1-C4-烷氧基-,羧基-C1-C4-烷氧基-,C1-C4-烷氧基-羰基-C1-C4-烷氧基-,C1-C4-烷基氨基羰基-C1-C4-烷氧基-,二-(C1-C4-烷基)-氨基羰基-C1-C4-烷氧基-,C1-C4-烷氧基-羰基-,C2-C4-键烯基氧基-,C2-C4-炔氧基-,C1-C4-烷硫基-,C1-C4-卤代烷硫基-,C1-C4-烷基亚磺酰基(sulphinyl)-,C1-C4-卤代烷基亚磺酰基-,C1-C4-烷基磺酰基-,C1-C4-卤代烷基磺酰基-,C1-C4-烷基-羰基-氨基-,C1-C4-烷氧基-羰基-氨基-或C1-C4-烷基-磺酰基-氨基-取代的含氮杂环基,上述杂环基选自吡咯基,吡唑基,咪唑基,三唑基,三唑啉基,吡啶基,吡嗪基,哒嗪基,嘧啶基,三嗪基,苯并噁唑基,苯并噻唑基,喹啉基(quinolinyl),喹唑啉基,喹喔啉基,
-包括通式(I)化合物的所有可能的互变异构体以及通式(I)化合物可能的盐和酸或碱加成化合物。
上述定义中,烃链,如烷基或烷二基,各自代表直链或支链-包括与杂原子连接的,如烷氧基。
上下文中给出的结构式中出现的优选的取代基或优选的基团范围如下所示。
Q优选代表O(氧),S(硫)或SO2,
R1优选代表氢,氨基,各自任选地被氰基-,氟-,氯-,甲氧基-或乙氧基-取代的甲基,乙基,正-或异丙基,或各自任选地被氟-和/或氯-取代的丙烯基或丙炔基,
R2优选代表氰基,羧基,氨基甲酰基,硫代氨基甲酰基或各自任选地被氰基-,氟-,氯-,甲氧基-或乙氧基-取代的甲基,乙基,正或异丙基,甲氧基羰基,乙氧基羰基,正或异丙氧基羰基,
R3优选代表氢,氟,氯,溴或各自任选地被氟-和/或氯-取代的甲基,乙基,正或异丙基,
R4优选代表氢,氰基,氟,氯或溴,
R5优选代表氰基,硫代氨基甲酰基,溴或各自任选地被氟-和/或氯-取代的甲基,乙基,甲氧基或乙氧基,
R6优选代表各自任选地被硝基-,羟基-,氨基-,氰基-,羧基-,氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正或异丙基-,正-,异-,仲或叔丁基-,氯甲基-,氟甲基-,二氯甲基-,二氟甲基-,三氯甲基-,三氟甲基-,氯二氟甲基-,氟二氯甲基-,氯乙基-,氟乙基-,二氯乙基-,二氟乙基-,氯氟乙基-,三氯乙基-,三氟乙基-,氯二氟乙基-,氟二氯乙基-,四氟乙基-,氯三氟乙基-,五氟乙基-,氯正丙基-,氟正丙基-,氯异丙基-,氟异丙基-,二氯丙基-,二氟丙基-,三氯丙基-,三氟丙基-,氰甲基-,氰乙基-,氰丙基-,羧甲基-,羧乙基-,羧丙基-,甲氧基甲基-,乙氧基甲基-,丙氧基甲基-,甲氧基乙基-,乙氧基乙基-,甲氧基羰基甲基-,乙氧基羰基甲基-,正或异丙氧基羰基甲基-,甲基氨基羰基甲基-,乙基氨基羰基甲基-,二甲基氨基羰基甲基-,甲氧基羰基乙基-,乙氧基羰基乙基-,正或异丙氧基羰基乙基-,甲氧基-,乙氧基-,正或异丙氧基-,正-,异-,仲或叔丁氧基-,二氟甲氧基-,三氟甲氧基-,氯二氟甲氧基-,羧基甲氧基-,羧基乙氧基-,甲氧基羰基甲氧基-,乙氧基羰基甲氧基-,正或异丙氧基羰基甲氧基-,甲基氨基羰基甲氧基-,乙基氨基羰基甲氧基-,二甲基氨基羰基甲氧基-,甲氧基羰基乙氧基-,乙氧基羰基乙氧基-,正或异丙氧基羰基乙氧基-,甲基氨基羰基乙氧基-,乙基氨基羰基乙氧基-,二甲基氨基羰基乙氧基-,甲氧基羰基-,乙氧基羰基-,正或异丙氧基羰基-,丙烯氧基-,丁烯氧基-,丙炔氧基-,丁炔氧基-,甲硫基-,乙硫基-,正或异丙硫基-,正-,异-,仲或叔丁硫基-,二氟甲硫基-,三氟甲硫基-,氯二氟甲硫基-,甲基亚磺酰基-,乙基亚磺酰基-,正或异丙基亚磺酰基-,三氟甲基亚磺酰基-,甲基磺酰基-,乙基磺酰基-,正或异丙基磺酰基-,三氟甲基磺酰基-,乙酰基氨基-,丙酰基氨基-,正或异丁酰基氨基-,甲氧基羰基氨基-,乙氧基羰基氨基-,正或异丙氧基羰基氨基-,甲基磺酰基氨基-,乙基磺酰基氨基-,正或异丙基磺酰基氨基-取代的含氮杂环基,上述杂环基选自吡咯基,吡唑基,咪唑基,三唑基,三唑啉基,吡啶基,吡嗪基,哒嗪基,嘧啶基,三嗪基,苯并噁唑基,苯并噻唑基,喹啉基,喹唑啉基,喹喔啉基,
Q特别优选代表O(氧)或S(硫),
R1特别优选代表氢,氨基或代表各自任选地被氟-,氯-,甲氧基-或乙氧基-取代的甲基或乙基,
R2特别优选代表氰基,羧基,氨基甲酰基或各自任选地被氟-和/或氯-取代的甲基,乙基,甲氧基羰基或乙氧基羰基,
R3特别优选代表氢,氟,氯,溴或各自任选地被氟-和/或氯-取代的甲基或乙基,
R4特别优选代表氢,氟或氯,
R5特别优选代表氰基,硫代氨基甲酰基,溴或三氟甲基,
R6特别优选代表各自任选地被硝基-,羟基-,氨基-,氰基-,羧基-,氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正或异丙基-,正-,异-,仲或叔丁基-,二氯甲基-,二氟甲基-,三氯甲基-,三氟甲基-,氯二氟甲基-,氟二氯甲基-,甲氧基-,乙氧基-,正或异丙氧基-,正-,异-,仲或叔丁氧基-,二氟甲氧基-,三氟甲氧基-,氯二氟甲氧基-,羧基甲氧基-,羧基乙氧基-,甲氧基羰基甲氧基-,乙氧基羰基甲氧基-,正或异丙氧基羰基甲氧基-,甲氧基羰基乙氧基-,乙氧基羰基乙氧基-,正或异丙氧基羰基乙氧基-,甲氧基羰基-,乙氧基羰基-,丙烯氧基-,丁烯氧基-,丙炔氧基-,丁炔氧基-,甲硫基-,乙硫基-,正或异丙硫基-,正-,异-,仲或叔丁硫基-,二氟甲硫基-,三氟甲硫基-,氯二氟甲硫基-,甲基亚磺酰基-,乙基亚磺酰基-,正或异丙基亚磺酰基-,三氟甲基亚磺酰基-,甲基磺酰基-,乙基磺酰基-,正或异丙基磺酰基-,三氟甲基磺酰基-,乙酰基氨基-,丙酰基氨基-,正或异丁酰基氨基-,甲氧基羰基氨基-,乙氧基羰基氨基-,正或异丙氧基羰基氨基-,甲基磺酰基氨基-,乙基磺酰基氨基-,正或异丙基磺酰基氨基-取代的含氮杂环基,上述杂环基选自吡咯基,吡唑基,咪唑基,三唑基,三唑啉基,吡啶基,吡嗪基,哒嗪基,嘧啶基,三嗪基,苯并噁唑基,苯并噻唑基,喹啉基,喹唑啉基,喹喔啉基,
Q更特别优选代表O(氧),
R1更特别优选代表氢,氨基,甲基或乙基,
R2更特别优选代表氰基或三氟甲基,
R3更特别优选代表氢,氯或甲基,
R5更特别优选代表氰基,硫代氨基甲酰基或溴,
R6更特别优选代表各自任选地被羟基-,氨基-,氰基-,羧基-,氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正或异丙基-,正-,异-,仲或叔丁基-,二氯甲基-,二氟甲基-,三氯甲基-,三氟甲基-,氯二氟甲基-,氟二氯甲基-,甲氧基-,乙氧基-,正或异丙氧基-,二氟甲氧基-,三氟甲氧基-,氯二氟甲氧基-,羧基甲氧基-,羧基乙氧基-,甲氧基羰基甲氧基-,乙氧基羰基甲氧基-,正或异丙氧基羰基甲氧基-,甲氧基羰基乙氧基-,乙氧基羰基乙氧基-,正或异丙氧基羰基乙氧基-,甲氧基羰基-,乙氧基羰基-,丙烯氧基-,丁烯氧基-,丙炔氧基-,丁炔氧基-,甲硫基-,乙硫基-,正或异丙硫基-,二氟甲硫基-,三氟甲硫基-,氯二氟甲硫基-,甲基亚磺酰基-,乙基亚磺酰基-,正或异丙基亚磺酰基-,三氟甲基亚磺酰基-,甲基磺酰基-,乙基磺酰基-,正或异丙基磺酰基-,三氟甲基磺酰基-,乙酰基氨基-,丙酰基氨基-,正或异丁酰基氨基-,甲氧基羰基氨基-,乙氧基羰基氨基-,正或异丙氧基羰基氨基-,甲基磺酰基氨基-,乙基磺酰基氨基-,正或异丙基磺酰基氨基-取代的吡唑基,吡啶基,嘧啶基,三嗪基或苯并噁唑基,
R1最优选代表氢,氨基或甲基,
R2最优选代表三氟甲基,
R5最优选代表氰基或溴,
R6最优选代表各自任选地被羟基-,氨基-,氰基-,氟-,氯-,甲基-,乙基-,三氯甲基-,甲氧基-或乙氧基-取代的吡唑基,吡啶基,嘧啶基或苯并噁唑基,
R6代表,尤其优选嘧啶基,
非常特别优选的一组化合物是下列那些式(I)化合物其中
Q代表O(氧),
R1代表甲基,
R2代表三氟甲基,
R3代表氢,氯或甲基,
R4代表氢,氟或氯,
R5代表氰基,以及
R6代表1-甲基-吡唑-5-基,1,3-二甲基-吡唑-5-基,1,3,4-三甲基-吡唑-5-基,1-甲基-3-三氟甲基-吡唑-5-基,1-乙基-吡唑-5-基,1-乙基-3-甲基-吡唑-5-基,1-乙基-3-三氟甲基-吡唑-5-基,1-正丙基-吡唑-5-基,1-正丙基-3-甲基-吡唑-5-基,1-正丙基-3-三氟甲基-吡唑-5-基,1-异丙基-吡唑-5-基,1-异丙基-3-甲基-吡唑-5-基,1-异丙基-3-三氟甲基-吡唑-5-基,1-正丁基-吡唑-5-基,1-异丁基-吡唑-5-基,1-仲丁基-吡唑-5-基或1-叔丁基-吡唑-5-基,
进一步非常特别优选的另一组化合物是下列那些式(I)化合物其中
Q代表O(氧),
R1代表甲基,
R2代表三氟甲基,
R3代表氢,氯或甲基,
R4代表氢,氟或氯,
R5代表溴,以及
R6代表1-甲基-吡唑-5-基,1,3-二甲基-吡唑-5-基,1,3,4-三甲基-吡唑-5-基,1-甲基-3-三氟甲基-吡唑-5-基,1-乙基-吡唑-5-基,1-乙基-3-甲基-吡唑-5-基,1-乙基-3-三氟甲基-吡唑-5-基,1-正丙基-吡唑-5-基,1-正丙基-3-甲基-吡唑-5-基,1-正丙基-3-三氟甲基-吡唑-5-基,1-异丙基-吡唑-5-基,1-异丙基-3-甲基-吡唑-5-基,1-异丙基-3-三氟甲基-吡唑-5-基,1-正丁基-吡唑-5-基,1-异丁基-吡唑-5-基,1-仲丁基-吡唑-5-基或1-叔丁基-吡唑-5-基,
更非常特别优选的另一组化合物是下列那些式(I)化合物其中
Q代表O(氧),
R1代表氨基,
R2代表三氟甲基,
R3代表氢,氯或甲基,
R4代表氢,氟或氯,
R5代表氰基,以及
R6代表1-甲基-吡唑-5-基,1,3-二甲基-吡唑-5-基,1,3,4-三甲基-吡唑-5-基,1-甲基-3-三氟甲基-吡唑-5-基,1-乙基-吡唑-5-基,1-乙基-3-甲基-吡唑-5-基,1-乙基-3-三氟甲基-吡唑-5-基,1-正丙基-吡唑-5-基,1-正丙基-3-甲基-吡唑-5-基,1-正丙基-3-三氟甲基-吡唑-5-基,1-异丙基-吡唑-5-基,1-异丙基-3-甲基-吡唑-5-基,1-异丙基-3-三氟甲基-吡唑-5-基,1-正丁基-吡唑-5-基,1-异丁基-吡唑-5-基,1-仲丁基-吡唑-5-基或1-叔丁基-吡唑-5-基,
另外更非常特别优选的另-组化合物是下列那些式(I)化合物其中
Q代表O(氧),
R1代表氨基,
R2代表三氟甲基,
R3代表氢,氯或甲基,
R4代表氢,氟或氯,
R5代表溴,以及
R6代表1-甲基-吡唑-5-基,1,3-二甲基-吡唑-5-基,1,3,4-三甲基-吡唑-5-基,1-甲基-3-三氟甲基-吡唑-5-基,1-乙基-吡唑-5-基,1-乙基-3-甲基-吡唑-5-基,1-乙基-3-三氟甲基-吡唑-5-基,1-正丙基-吡唑-5-基,1-正丙基-3-甲基-吡唑-5-基,1-正丙基-3-三氟甲基-吡唑-5-基,1-异丙基-吡唑-5-基,1-异丙基-3-甲基-吡唑-5-基,1-异丙基-3-三氟甲基-吡唑-5-基,1-正丁基-吡唑-5-基,1-异丁基-吡唑-5-基,1-仲丁基-吡唑-5-基或1-叔丁基-吡唑-5-基,
更加非常特别优选的另一组化合物是下列那些式(I)化合物其中
Q,R1,R2,R3,R4和R5代表上述定义以及
R6代表嘧啶-2-基,5-氯-嘧啶-2-基,5-氟-嘧啶-2-基,4,5-二氯-嘧啶-2-基,4,5-二氟-嘧啶-2-基,4-氯-5-氟-嘧啶-2-基,4-甲基-嘧啶-2-基,4,6-二甲基-嘧啶-2-基,4-甲基-6-三氟甲基-嘧啶-2-基,5-氯-4,6-二甲基-嘧啶-2-基,5-氟-4,6-二甲基-嘧啶-2-基,4,5,6-三甲基-嘧啶-2-基,4-甲氧基-6-甲基-嘧啶-2-基,6-二氟甲氧基-4-甲基-嘧啶-2-基,4-甲氧基-6-三氟甲基-嘧啶-2-基,4,6-二甲氧基-嘧啶-2-基,嘧啶-4-基,6-氯-嘧啶-4-基,5,6-二氯-嘧啶-4-基,6-氯-5-氟-嘧啶-4-基,6-甲基-嘧啶-4-基,5-氯-6-甲基-嘧啶-4-基,6-三氟甲基-嘧啶-4-基,6-羟基-嘧啶-4-基,6-甲氧基-嘧啶-4-基,6-甲氧基羰基甲氧基-嘧啶-4-基,6-乙氧基羰基甲氧基-嘧啶-4-基,6-甲氧基羰基乙氧基-嘧啶-4-基,6-乙氧基羰基乙氧基-嘧啶-4-基,6-氯-5-氟-嘧啶-4-基,5-氟-4-羟基-嘧啶-4-基或5-氟-6-甲氧基-嘧啶-4-基,
更加非常特别优选的另一组化合物是下列那些式(I)化合物其中
Q,R1,R2,R3,R4和R5代表上述定义以及
R6代表吡啶-2-基,吡啶-3-基,吡啶-4-基,3-氯-吡啶-2-基,3-氟-吡啶-2-基,4-氯-吡啶-2-基,4--吡啶-2-基,5-氯-吡啶-2-基,5-氟-吡啶-2-基,3,4-二氯-吡啶-2-基,3,5-二氯-吡啶-2-基,3,6-二氯-吡啶-2-基,3,4-二氟-吡啶-2-基,3,5-二氟-吡啶-2-基,3,6-二氟-吡啶-2-基,3,5,6-三氯-吡啶-2-基,3,5,6-三氟-吡啶-2-基,3-氰基-吡啶-2-基,4-氰基-吡啶-2-基,5-氰基-吡啶-2-基,6-氰基-吡啶-2-基,3-甲基-吡啶-2-基,4-甲基-吡啶-2-基,5-甲基-吡啶-2-基,6-甲基-吡啶-2-基,4-氯-吡啶-3-基,4-氟-吡啶-3-基,5-氯-吡啶-3-基,5-氟-吡啶-3-基,6-氯-吡啶-3-基,6-氟-吡啶-3-基,4,5-二氯-吡啶-3-基,4,5-二氟-吡啶-3-基,2-氰基-吡啶-3-基,4-氰基-吡啶-3-基,5-氰基-吡啶-3-基,6-氰基-吡啶-3-基,2-甲基-吡啶-3-基,4-甲基-吡啶-3-基,5-甲基-吡啶-3-基,6-甲基-吡啶-3-基,2-氯-吡啶-4-基,2-氟-吡啶-4-基,3-氯-吡啶-4-基,3-氟-吡啶-4-基,2-氰基-吡啶-4-基,3-氰基-吡啶-4-基,2-甲基-吡啶-4-基或3-甲基-吡啶-4-基,
更加非常特别优选的另-组化合物是下列那些式(I)化合物其中
Q,R1,R2,R3,R4和R5代表上述定义以及
R6代表嘧啶-2-基,5-氯-嘧啶-2-基,5-氟-嘧啶-2-基,4,5-二氯-嘧啶-2-基,4,5-二氟-嘧啶-2-基,4-氯-5-氟-嘧啶-2-基,4-甲基-嘧啶-2-基,4,6-二甲基-嘧啶-2-基,4-甲基-6-三氟甲基-嘧啶-2-基,5-氯-4,6-二甲基-嘧啶-2-基,5-氟-4,6-二甲基-嘧啶-2-基,4,5,6-三甲基-嘧啶-2-基,4-甲氧基-6-甲基-嘧啶-2-基,6-二氟甲氧基-4-甲基-嘧啶-2-基,4-甲氧基-6-三氟甲基-嘧啶-2-基,4,6-二甲氧基-嘧啶-2-基。
本发明优选其中包括上述优选定义的组合的那些式(I)化合物。
本发明特别优选其中包括上述特别优选定义的组合的那些式(I)化合物。
本发明更特别优选其中包括上述更特别优选定义的组合的那些式(I)化合物。
本发明最优选其中包括上述最优选定义的组合的那些式(I)化合物。
上述一般或优选基团定义既适用于式(I)终产物,也相应适用于制备各自化合物所需起始物或中间体。这些基团定义可按需要互相组合,即包括上述所给优选范围之间的组合。
新的通式(I)的取代的苯基尿嘧啶类具有有益的生物活性。特别是,它们具有很强的除草活性。
新的通式(I)的取代的苯基尿嘧啶类是通过下述方法制备
(a)如适合在反应助剂存在下以及如适合在稀释剂存在下,
使通式(II)的苯基尿嘧啶类
其中
Q,R1,R2,R3,R4和R5各自如上定义
与通式(III)化合物反应制备
X1-R6 (III)
其中
R6如上定义以及
X1代表卤素或烷基磺酰基,
或
(b)如适合在反应助剂存在下以及如适合在稀释剂存在下,
使通式(IV)的卤代苯基尿嘧啶类
其中
R1,R2,R3,R4和R5各自如上定义以及
X2代表卤素,
与通式(V)化合物反应制备
M-Q-R6 (V)
其中
Q和R6各自如上定义以及
M代表氢或等价金属,
或
(c)如适合在反应助剂存在下以及如适合在稀释剂存在下,
使通式(VI)的氨基链烯酸酯
其中
R1,R2和R3各自如上定义以及
R代表烷基,芳基或芳烷基,
其中
Q,R4,R5和R6各自如上定义
或与通式(VIII)的取代的苯基氨基甲酸酯类(phenyl urethane)(苯基氨基甲酸酯)反应制备
其中
Q,R4,R5和R6各自如上定义以及
R代表烷基,芳基或芳烷基,
或
(d)在水存在下以及如适合在有机溶剂存在下,
其中
Q,R4,R5和R6各自如上定义以及
R′代表烷基
或
(e)如适合在反应助剂存在下以及如适合在稀释剂存在下,
使通式(Ia)的取代的苯基尿嘧啶类
其中
Q,R2,R3,R4,R5和R6各自如上定义
与1-氨基氧基-2,4-二硝基-苯或2-氨基氧基磺酰基-1,3,5-三甲基苯或与通式(X)的烷基化试剂反应进行制备
X3-A1 (X)
其中
A1代表任选地被氰基-,卤素-或C1-C4-烷氧基-取代的带有1-4个碳原子的烷基或各自任选的卤素取代的各自带有2-4个碳原子的链烯基或炔基,以及
X3代表卤素或基团-O-SO2-O-A1,
以及如适合随后以常规方式进行取代基定义范围内的亲电子或亲核和/或氧化或还原反应。
可通过常规方法使通式(I)化合物转化为如上述定义的其它通式(I)化合物,例如通过与氰气或硫化氢反应(例如R5: , ,参见制备实施例)。
例如,使用3-氨基-1-(2-氯-4-溴-5-羟基-苯基)-4-三氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶和4-二氟甲氧基-6-甲基-2-甲基磺酰基-嘧啶作为起始物,按本发明方法(a)的反应步骤可通过下述反应路线解释:
例如,使用1-(4-氰基-2,5-二氟-苯基)-4-氯二氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶和5-羟基-1-甲基-吡唑作为起始物,按本发明方法(b)的反应步骤可通过下述反应路线解释:
例如,使用[1-[4-氰基-2-氟-5-(嘧啶-2-基)-苯基]-2,5-二氧代-2,5-二氢-1H-吡咯-3-基]-氨基甲酸甲酯作为起始物,按本发明方法(d)的反应步骤可通过下述反应路线解释:
例如,使用1-[4-氰基-2-氟-5-(1,3-二甲基-吡唑-5-基-氧基)-苯基]-4-二氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶和溴代甲烷作为起始物,按本发明方法(e)的反应步骤可通过下述反应路线解释:
式(II)代表在用于制备式(I)化合物的本发明方法(a)中用作起始物的苯基尿嘧啶类的通式。在式(II)中,Q,R1,R2,R3,R4和R5各自优选或特别代表前面已列出的,涉及本发明通式(I)化合物定义中作为Q,R1,R2,R3,R4和R5的优选或特别优选的那些定义。
通式(II)的起始物是已知的和/或可通过本身已知的方法制备(参见WO-A-97/01541,WO-A-98/54155)。
通式(III)代表在本发明方法中还可用作起始物的另一些化合物的通式。在通式(III)中,R6优选代表前面已列出的,涉及本发明通式(I)化合物定义中作为R6的优选、特别优选、更特别优选或最优选的那些定义;X1优选代表氟,氯,溴,碘或带有1-3个碳原子的烷基磺酰基,特别是氟,氯,溴或甲基磺酰基。
大多数通式(III)的起始物都是已知的用于合成的有机化合物。
式(IV)代表在用于制备通式(I)化合物的本发明方法(d)中用作起始物的卤代苯基尿嘧啶类的通式。在通式(IV)中,R1,R2,R3,R4和R5各自优选代表前面已列出的,涉及本发明通式(I)化合物定义中作为R1,R2,R3,R4和R5的优选、特别优选、更特别优选或最优选的那些定义;X2优选代表氟,氯和溴,特别是氟或氯。
通式(IV)的起始物是已知的和/或可通过本身已知的方法制备(参见EP-A-648749)。
式(V)代表在本发明方法(b)中还可用作起始物的化合物的通式。在通式(V)中,Q和R6各自优选代表前面已列出的涉及本发明通式(I)化合物定义中作为Q和R6的优选、特别优选、更特别优选或最优选的那些定义;M优选代表氢或碱金属,特别是氢,钠或钾。
大多数通式(V)的起始物都是已知的用于合成的有机化合物。
式(VI)代表在用于制备通式(I)化合物的本发明方法(c)中用作起始物的氨基链烯酸酯的通式。在通式(VI)中,R1,R2和R3各自优选代表,前面已列出的涉及本发明通式(I)化合物定义中作为R1,R2和R3的优选、特别优选、更特别优选或最优选的那些定义;R优选代表C1-C4-烷基,苯基或苄基,特别是甲基或乙基。
通式(VI)的起始物是已知的和/或可通过本身已知的方法制备(参见J.Heterocycl.Chem.9(1972),513-522)。
式(VII)代表在本发明方法(c)中还可用作起始物的异氰酸苯酯的通式以及通式(VIII)代表另一用作起始物的苯基氨基甲酸酯的通式。在通式(VII)和(VIII)中,Q,R4,R5和R6各自优选代表,前面已列出的涉及本发明通式(I)化合物定义中作为Q,R4,R5和R6的优选、特别优选、更特别优选或最优选的那些定义;R优选代表C1-C4-烷基,苯基或苄基,特别是甲基,乙基,苯基或苄基。
迄今文献中尚未公开通式(VII)和(VIII)的起始物,作为新物质,它们也构成了本发明主题的一部分。
新的通式(VII)的取代的异氰酸苯酯可通过下述方法制备:
在存在稀释剂,如,例如氯苯,温度为-20℃至+150℃的条件下(还可参见EP-A-648749),
使通式(XI)的苯胺衍生物与光气反应制备
其中
Q,R4,R5和R6各自如上定义。
新的通式(VIII)的取代的苯基氨基甲酸酯可通过下述方法制备:
如适合存在酸性接受体,例如吡啶,以及如适合存在稀释剂,例如二氯甲烷,并在-20℃至+100℃的条件下(参见制备实施例)
使通式(XI)的苯胺衍生物
其中
Q,R4,R5和R6各自如上定义,
与通式(XII)的氯羰基化合物反应制备
RO-CO-Cl (XII)
其中
R如上定义。
作为前体的通式(XI)的苯胺衍生物通常是已知的和/或可通过本身已知的方法(参见DE-A-3240975,DE-A-3337828,EP-A-79311)。
目前尚未公开过的,作为新物质的通式(XIa)的苯胺衍生物是本申请主题的一部分
其中
Q,R4和R6各自如上定义以及,
Y代表氰基,硫代氨基甲酰基或三氟甲基。
新的通式(XIa)的苯胺衍生物通过下述方法制备:
其中
Q,R4和Y各自如上定义
与通式(III)化合物反应
X1-R6 (III)
其中
R6和X1各自如上定义,
如适合存在酸性接受体,例如氢氧化钾,碳酸钾或吡啶,以及如适合存在稀释剂,例如甲醇,乙腈,N,N-二甲基甲酰胺或N-甲基吡咯烷酮,并在0℃至200℃条件下进行反应(参见制备实施例)。
或
(β)使通式(XIV)的苯胺
其中
R4,X2和Y各自如上定义
与通式(V)化合物反应
M-Q-R6 (V)
其中
M,Q和R6各自如上定义,
如适合存在酸性接受体,例如碳酸钾或氢化钠,以及如适合存在稀释剂,例如乙腈,N,N-二甲基甲酰胺或N-甲基吡咯烷酮,并在0℃至200℃条件下进行反应(参见制备实施例)。
式(IX)代表在用于制备通式(I)化合物的本发明方法(d)中用作起始物的取代的N-苯基-1-烷氧基羰基氨基-马来酰亚胺的通式。在通式(IX)中,Q,R4,R5和R6各自优选代表,前面已列出的涉及本发明通式(I)化合物定义中作为Q,R4,R5和R6的优选、特别优选、更特别优选或最优选的那些定义;R′优选代表C1-C4-烷基,特别是甲基或乙基。
新的通式(IX)的取代的N-苯基-1-烷氧基羰基氨基-马来酰亚胺是通过下述方法制备的
如适合在存在稀释剂,例如乙酸,并在温度为0℃-200℃的条件下,
使通式(XV)的(2,5-二氧代-2,5-二氢-呋喃-3-基)-氨基甲酸烷基酯
其中
R3如上定义以及
R’代表烷基(特别是甲基或乙基)
与通式(XI)的苯胺衍生物反应
其中
Q,R4,R5和R6各自如上定义。
通式(XV)的前体是已知的和/或由本身已知方法制备(参见DE-A-19604229)。
式(Ia)代表在用于制备通式(I)化合物的本发明方法(e)中用作起始物的取代的苯基尿嘧啶类的通式。在通式(Ia)中,Q,R2,R3,R4,R5和R6各自优选或特别代表,前面已列出的涉及本发明通式(I)化合物定义中作为Q,R2,R3,R4,R5和R6的优选或特别优选的那些定义。
作为新物质,方法(e)中的通式(Ia)的起始物也构成本申请主题的一部分;它们可通过本发明方法(a)-(d)制备。
式(X)代表在本发明方法(e)中还可用作起始物的烷基化试剂的通式。在通式(X)中,A1优选代表各自可选择地被氰基-,氟-,氯-,甲氧基-或乙氧基-取代的甲基,乙基,正或异丙基或各自可选择地被氟-和/或氯-取代的丙烯基或丙炔基,特别是甲基或乙基;X3优选代表氯,溴,碘,甲氧基磺酰氧基或乙氧基磺酰氧基,特别是溴或甲氧基磺酰氧基。
起始物通式(X)是已知的用于合成的有机化合物。
制备通式(I)化合物的本发明方法优选在使用稀释剂的条件下进行。除了水之外,适用于本发明方法(a),(b),(c),(d)和(e)的稀释剂特别是惰性有机溶剂。这些有机溶剂特别包括脂族、脂环族或芳族的,并任选卤代烃,如汽油(benzine)、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚类如二乙醚、二异丙基醚、二噁烷、四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;酮类如丙酮、丁酮或甲基异丁酮;腈如乙腈、丙腈或丁腈;酰胺如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺;酯类如乙酸甲酯或乙酸乙酯;亚砜如二甲基亚砜;醇类如甲醇、乙醇、正或异丙醇、乙二醇单甲醚、乙二醇单乙醚、二甘醇单甲醚、二甘醇单乙醚,它们与水或纯水的混合物。
适用于本发明方法(a),(b),(c)和(e)的反应助剂,一般为常规的无机或有机碱或酸性接受体。这些物质优选包括碱金属或碱土金属的乙酸盐,酰胺,碳酸盐,碳酸氢盐,氢化物,氢氧化物或醇盐,例如乙酸钠,乙酸钾或乙酸钙,氨基化锂,氨基化钠,氨基化钾或氨基化钙,碳酸钠,碳酸钾或碳酸钙,碳酸氢钠,碳酸氢钾或碳酸氢钙,氢化锂,氢化钠,氢化钾或氢化钙,氢氧化锂,氢氧化钠,氢氧化钾或氢氧化钙,甲醇钠,乙醇钠,正或异丙醇钠,正-、异-、仲-或叔丁醇钠或甲醇钾,乙醇钾,正或异丙醇钾,正-、异-、仲-或叔丁醇钾;另外还包括碱性有机氮化合物,例如三甲胺,三乙胺,三丙胺,三丁胺,乙基-二异丙胺,N,N-二甲基-环己胺,二环己胺,乙基-二环己胺,N,N-二甲基-苯胺,N,N-二甲基苄胺,吡啶,2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基-和3,5-二甲基吡啶,5-乙基-2-甲基-吡啶,4-二甲基氨基吡啶,N-甲基-哌啶,1,4-二氮杂二环[2.2.2]辛烷(DABCO),1,5-二氮杂二环[4.3.0]壬-5-烯(DBN)或1,8-二氮杂二环[5.4.0]十一-7-烯(DBU)。
适于本发明方法(a),(b),(c)和(e)的另一些反应助剂是相转移催化剂。可提及的上述催化剂的实例是:
溴化四丁基铵、氯化四丁基铵、氯化四辛基铵、硫酸氢四丁基铵、氯化甲基三辛基铵、氯化十六烷基三甲基铵、溴化十六烷基三甲基铵、氯化苄基三甲基铵、氯化苄基三乙基铵、氢氧化苄基三甲基铵、氢氧化苄基三乙基铵、氯化苄基三丁基铵、溴化苄基三丁基铵、溴化四丁基鏻、氯化四丁基鏻、溴化三丁基十六烷基鏻、氯化丁基三苯基鏻、溴化乙基三辛基鏻、溴化四苯基鏻。
本发明方法(d)中优选使用的金属氢氧化物是碱金属或碱土金属氢氧化物,特别是氢氧化锂,氢氧化钠,氢氧化钾或氢氧化钙。
当进行本发明制备方法(a),(b),(c),(d)和(e)时,反应温度可在很宽的范围内变化。通常,本发明方法在0℃至150℃,优选10℃至120℃下进行。
通常本发明方法(a),(b),(c),(d)和(e)是在大气压下进行。然而,本发明方法也可以在高压或减压-一般在0.1bar至10bar的条件下进行反应。
当采用本发明制备方法时,起始物通常使用近似等摩尔量。然而,还可以相对较多过量使用其中一种组分。通常,反应是在存在反应助剂的条件下在适合的稀释剂中进行,并且通常将反应混合物在所需温度下搅拌几小时。通过常规方法进行处理(参见制备实施例)。
本发明活性化合物可用作脱叶剂,干燥剂,除草秆剂,特别是除草剂。从广义上讲,杂草应理解为生长在不适合场所的所有植物。本发明物质是否用作灭生性或选择性除草剂基本上是根据其使用量而确定。
本发明的活性化合物例如可用于下述植物:
双子叶杂草属:苘麻属,苋属,豚草属,单花葵属,春黄菊属,Aphanes,滨藜属,雏菊属,鬼针草属,荠菜属,飞廉属,决明属,矢车菊属,藜属,蓟属,旋花属,曼陀罗属,金钱草,刺酸模属,糖芥属,大戟属,鼬瓣花属,牛膝菊属,猪殃殃属,木槿属,番薯属,地肤属,野芝麻属,独行菜属,母草属,母菊属,薄荷属,山靛属,Mullugo,勿忘草属,罂粟属,牵牛属,车前属,蓼属,马齿苋属,毛茛属,萝卜属,菜属,水松叶属,酸模属,猪毛菜属,千里光属,田菁属,黄花稔属,欧白芥属,茄属,苦苣菜属,尖瓣花属,繁缕属,蒲公英属,遏蓝菜属,车轴草属,荨麻属,婆婆纳属,堇菜属,苍耳属。
双子叶作物属:花生属,甜菜属,芸苔属,黄瓜属,南瓜属,向日葵属,胡萝卜属,大豆属,棉属,甘薯属,莴苣属,亚麻属,番茄属,烟草属,菜豆属,豌豆属,茄属,巢菜属。
单子叶杂草属:山羊草属,冰草属,翦股颍属,看麦娘属,假翦股颍属,燕麦属,臂形草属,雀麦属,蒺藜草属,鸭跖草属,狗牙根属,莎草属,龙爪茅属,马唐属,稗属,荸荠属,蟋蟀草属,画眉草属,野黍属,羊茅属,飘拂草属,异蕊花属,白茅属,鸭嘴草属,千金子属,毒麦属,雨久花属,黍属,雀稗属,草属,梯牧草属,早熟禾属,筒轴茅属,慈菇属,草属,狗尾草属,高粱属。
单子叶作物属:葱属,菠萝,天门冬属,燕麦属,大麦属,稻属,黍属,甘蔗属,黑麦属,高粱属,黑小麦,小麦,玉米属。
然而,本发明活性化合物的应用不限制于上述各属,还可以同样方式扩展至其它植物。
根据其浓度,本发明活性化合物适合于灭生性地防治杂草,例如在工业区和铁轨,种树或没种树的路或区域。同样,本发明化合物还可用来防治多年生作物中的杂草,例如森林,观赏树木,果园,葡萄园,柑桔园,坚果园,香蕉园,咖啡园,茶园,橡胶园,油棕园,可可园,浆果种植园和啤酒花栽培区,草皮,草坪和牧草中的杂草,还可选择性地防除一年生作物中的杂草。
当本发明的式(I)化合物应用于土壤和植物的地上部分时表现出很强的除草活性且作用谱广。在某种程度上,本发明式(I)化合物还适合于在单子叶和双子叶作物中,通过苗前或苗后方法选择性地防治单子叶和双子叶杂草。
在一定浓度或使用量时,本发明活性化合物还可用于控制害虫以及真菌性或细菌性植物病害。如需要,它们还可用作合成其它活性化合物的中间体或母体。
根据本发明,可以处理所有植物以及植物各部分。此处植物可以理解为表示所有植物以及植物群落如需要和不需要的野生植物或作物(包括天然长出的作物)。作物可以是通过常规育种和优化方法或通过生物技术和遗传工程方法或上述方法的结合获得的植物,包括转基因植物以及包括获得或没有获得植物育种者证书(plantbreeders’certificates)保护的植物栽培品种。植物的各部分可理解为所有地上和地下部分以及植物器官如茎、叶、花和根,可提及的实例为叶片、针叶、枝条、树干、花、子实体、果实和种子以及根、块茎和根状茎。植物各部分还包括收获的植物和植物营养体以及有性繁殖材料,例如种苗、块茎、根状经、插条和种子。
使用本发明活性化合物进行植物和植物各部分的处理是通过常规处理方法直接施用或作用于它们的环境、生境或贮藏区进行处理,例如通过浸渍、喷雾、熏蒸、弥雾、撒播、刷涂以及在繁殖材料特别是种子的情况下还可以进行一层或多层包衣。
本发明活性化合物可被转化成为常规的制剂,如液剂,乳剂,可湿性粉剂,悬浮剂,粉剂,细粉剂,糊剂,可溶粉剂,颗粒剂,浓悬浮乳剂,用活性化合物浸渍的天然和合成材料以及聚合物包封的微胶囊剂。
这些制剂是以已知方法生产的,例如通过将活性化合物与填充剂,即液体溶剂和/或固体载体混合而生产,制剂中可选择使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适当的液体溶剂主要有:芳香烃类,如二甲苯,甲苯或烷基萘,氯代芳烃类和氯代脂肪烃类,如氯苯,二氯乙烷或二氯甲烷,脂肪烃类,如环己烷或链烷烃,例如石油馏份,矿物油和植物油,醇类,如丁醇或乙二醇及其醚和酯类,酮类,如丙酮,甲基乙基酮,甲基异丁基酮或环己酮,强极性溶剂如二甲基甲酰胺和二甲基亚砜以及水。
适当的固体载体有:例如,铵盐和天然矿物粉末,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅,氧化铝和硅酸盐;适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石,大理石,浮石,海泡石,白云石,以及无机的合成颗粒和有机粉末,和有机材料的颗粒如锯末,坚果壳,玉米穗茎和烟草茎;适当的乳化剂和/或发泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如木质素亚硫酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素,粉末、颗粒或胶乳状天然或合成聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂,和合成磷脂。其它可能的添加剂是矿物油和植物油。
可以使用的着色剂如无机颜料,例如氧化铁,氧化钛,普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和痕量营养物如金属盐,例如,铁、锰、硼、铜、钴、钼和锌盐。
制剂中通常含有按重量计0.1-95%,优选0.5-90%的活性化合物。
在防治杂草时,本发明的活性化合物可以其本身或制剂形式使用,还可以与已知除草剂和/或改进与作物相容性的物质(“安全剂”)的混合物形式,成品制剂或桶混方式使用。还可以与包括一种或多种已知除草剂和安全剂的除草剂混合制成混合物。
可用于混合物中的适合的组分都是已知除草剂,例如
乙草胺、三氟羧草醚(-钠)、苯草醚、甲草胺、禾草灭(-钠)、莠灭净、amicarbazone、先甲草胺、酰嘧磺隆、莎稗磷、磺草灵、莠去津、唑啶炔草、四唑嘧磺隆、beflubutamid、草除灵(-乙酯)、呋草黄、苄嘧磺隆(-甲酯)、噻草平、benzfendizone、benzobicyclon、吡草酮、新燕灵(-乙酯)、双丙氨膦、甲羧除草醚、双草醚(-钠)、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、butafenacil(-烯丙酯)、丁氧环酮、丁草敌、苯酮唑、醌肟草、双酰草胺、氟酮唑草(-乙酯)、甲氧除草醚、草灭畏、氯草敏、氯嘧磺隆(-乙酯)、草枯醚、氯磺隆、绿麦隆、cinidon(-乙酯)、环庚草醚、醚黄隆、clefoxydim、烯草酮、炔草酸(-炔丙酯)、异恶草松、氯甲酰草胺、二氯吡啶酸、clopyrasulfuron(-甲酯)、唑嘧磺胺盐(-甲酯)、cumyluron、氰草津、cybutryne、环草敌、环丙嘧磺隆、噻草酮、氰氟草酯(-丁酯)、2,4-滴、2,4-滴丁酸、甜菜安、燕麦敌、麦草畏、精2,4-滴丙酸(-P)、禾草灵(-甲酯)、唑嘧磺胺、乙酰甲草胺(-乙酯)、野燕枯、吡氟酰草胺、二氟吡隆、恶唑隆、哌草丹、二甲草胺、异戊乙净、二甲吩草胺、dimexyflam、敌乐胺、双苯酰草胺、敌草快、氟硫草啶、敌草隆、杀草隆、epoprodan、扑草灭(EPTC)、戊草丹、乙丁烯氟灵、胺苯磺隆(-甲酯)、乙氧呋草黄、ethoxyfen、乙氧嘧磺隆、乙苯酰草、精恶唑禾草灵(-P,-乙酯)、fentrazamide、麦草氟异丙酯(麦草氟异丙酯-L、麦草氟甲酯)、啶嘧磺隆、florasulam、精吡氟禾草灵(-P,-丁酯)、fluazolate、flucarbazone(-钠盐)、flufenacet、氟唑啶草、氟烯草酸(-戊酯)、丙炔氟草胺、flumipropyn、唑嘧磺草胺、氟草隆、氟咯草酮、乙羧氟草醚(-乙酯)、氟胺草唑、flupropacil、flurpyrsulfuron(-甲酯,-钠盐)、芴丁酯、氟啶草酮、氯氟吡氧乙酸(-丁氧丙酯,-甲基庚基酯)、氟嘧醇、呋草酮、达草氟(-甲酯)、噻唑草酰胺、氟磺胺草醚、foramsulfuron、草铵膦(铵盐)、草甘膦异丙胺盐、氟硝磺酰胺、氟吡氯禾灵、精氟吡甲禾灵、环嗪酮、咪草酯(-甲酯)、imazamethapyr、咪草啶酸、imazapic、咪唑烟酸、咪唑喹啉酸、咪唑乙烟酸、咪吡嘧磺隆、iodosulfuron(-甲酯,钠盐)、碘苯腈、异丙乐灵、异丙隆、异恶隆、异噁草胺、isoxachlortole、异噁氟草、异恶草醚、乳氟禾草灵、环草啶、利谷隆、2甲4氯、2甲4氯丙酸、苯噻酰草胺、mesotrione、苯嗪草酮、吡唑草胺、甲基苯噻隆、吡喃隆、溴谷隆、(α-)异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲磺隆(-甲酯)、禾草敌、绿谷隆、萘丙胺、敌草胺、草不隆、烟嘧磺隆、氟草敏、坪草丹、氨磺乐灵、炔丙噁唑草、恶草灵、环丙氧磺隆、氯噁嗪草、乙氧氟草醚、百草枯、壬酸、二甲戊灵、pendralin、戊噁唑草、甜菜宁、picolinafon、哌草磷、丙草胺、氟嘧磺隆(-甲酯)、profluazol、扑草净、毒草胺、敌稗、恶草酸、异丙草胺、propoxycarbazone(-钠盐)、炔苯酰草胺、苄草丹、氟磺隆、氟唑草酯(-乙酯)、pyrazogyl、吡唑特、吡嘧磺隆(-乙酯)、苄草唑、pyribenzoxim、稗草丹、哒草特、pyridatol、pyriftalid、肟啶草(-甲酯)、嘧草硫醚(-钠)、二氯喹啉酸、氯甲喹啉酸、灭藻醌、精喹禾灵(-p-乙酯,-P-tefuryl)、喹禾糖酯、砜嘧磺隆、稀禾啶、西玛津、西草净、磺草酮、甲磺草胺、甲嘧磺隆(-甲酯)、草硫磷、乙黄黄隆、牧草胺、丁噻隆、tepraloxydim、特丁津、特丁净、噻吩草胺、thiafluamide、噻唑烟酸、噻二唑胺、噻吩磺隆(-甲酯)、禾草丹、仲草丹、三甲苯草酮、野麦畏、醚苯磺隆、苯磺隆、三氯吡氧乙酸、灭草环、氟乐灵、trifloxysulfuron、氟胺磺隆(-甲酯)和tritosulfuron。
还可以与其它已知活性化合物如杀真菌剂,杀虫剂,杀螨剂,杀线虫剂,驱鸟剂,植物营养剂和土壤结构改良剂混合。
本发明活性化合物可以其本身或其制剂形式或进一步稀释制备的应用形式使用,如现用溶液,悬浮液,乳液,粉剂,糊剂或颗粒剂。可以常规方式例如灌水,喷雾,弥雾或撒播方式使用上述制剂。
可在植物苗前或苗后使用本发明活性化合物。还可在播种前将活性化合物施入土壤。
使用的活性化合物的量可在相当宽的范围内变化。这要根据所需作用的性质而确定。通常,用量为对每公顷土表使用1g至10kg活性化合物,优选每公顷5g至5kg活性化合物。
通过下述实施例解释本发明活性化合物的制备和应用。
制备实施例:
实施例1
(方法(c))
使1.03g(5.6mmol)的3-氨基-4,4,4-三氟巴豆酸甲酯加入冷却至0℃的含有0.28g(7mmol)氢化钠(60%浓度的矿物油分散体)的10mlN,N-二甲基甲酰胺混合物中。搅拌下将混合物加温至室温(约20℃),然后逐滴加入含2.0g(5.62mol)的N-[4-溴-2-氟-5-(嘧啶-2-基-氧基)-苯基]-氨基甲酸O-乙酯的25ml N,N-二甲基甲酰胺溶液。将反应混合物在150℃下加热6小时。然后将混合物倒入300ml的2N盐酸中,加入近似等体积的二乙醚和石油醚1∶1混合物并将混合物搅拌约3小时。将所得结晶状产物通过抽滤分离。
由此获得1.6g(理论值的64%)的1-[4-溴-2-氟-5-(嘧啶-2-基-氧基)-苯基]-4-三氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶。
LogP=1.96a)
实施例2
(方法(e))
室温下,向1.35g(3.0mmol)1-[4-溴-2-氟-5-(嘧啶-2-基-氧基)-苯基]-4-三氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶,0.84g(6.0mmol)碳酸钾和25ml乙腈的混合物中边搅拌边逐滴加入0.46g(3.6mmol)的硫酸二甲酯,将反应混合物回流条件下加热2小时。将混合物冷却至室温,用水稀释至原始体积的约两倍,然后用二氯甲烷萃取三次。将合并的有机相用硫酸钠干燥并过滤。在水泵抽真空条件下浓缩滤液并将剩余物溶解在乙酸乙酯中然后通过硅胶抽吸过滤。在水泵抽真空条件下浓缩滤液,残余物用二乙醚消解(digest)并通过抽滤分离获得结晶状产物。
由此获得0.70g(理论值的51%)的1-[4-溴-2-氟-5-(嘧啶-2-基-氧基)-苯基]-3-甲基-4-三氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶。
LogP=2.47a)。
类似于实施例1和2,并根据本发明制备方法的一般性描述,还可以制备,例如下表1中所列的通式(I)化合物。
表1中给出的logP值是根据EEC Directive 79/831 Annex V.A8方法通过HPLC(高效液相色谱)使用反相柱(C18),温度为43℃的条件下确定的。
(a)在酸性条件下用于测定的流动相:0.1%磷酸水溶液,乙腈;10%乙腈至90%乙腈的线性梯度-对应的测试结果在表1中以a)标记。
(b)在中性条件下用于测定的流动相:0.01摩尔磷酸盐缓冲液,乙腈;10%乙腈至90%乙腈的线性梯度-对应的测试结果在表1中以b)标记。
使用具有已知logP值的直链烷-2-酮(具有3-16个碳原子)进行校定(通过两个连续的链烷酮之间的线性内插值的保留时间测定logP值)。
使用200-400nm的UV光谱在色谱信号最大值中确定λmax。
制备如实施例4的表1所列化合物,例如,制备方法如下:
(方法(a))
使0.50g(1.5mmol)的1-(4-氰基-2-氟-5-羟基-苯基)-3-甲基-4-三氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶,0.30g(2.2mmol)的碳酸钾和50ml二甲基亚砜的混合物在室温(约20℃)下搅拌15分钟。加入0.36g(1.7mmol)的4,6-二甲氧基-2-甲基磺酰基-嘧啶,然后将反应混合物在60℃搅拌3小时,然后在90℃搅拌8小时,室温下再搅拌12小时,90℃再搅拌12小时,最后室温下搅拌12小时。然后将混合物倒入饱和的氯化钠水溶液中并用乙酸乙酯萃取,将有机相先用水再用饱和的氯化钠水溶液洗涤,用硫酸钠干燥并过滤。在水泵抽真空条件下浓缩滤液,将残余物消解在二乙基乙基/二异丙基醚中,通过抽分离得到结晶状产物。
由此获得0.20g(理论值的29%)的1-[4-氰基-2-氟-5-(4,6-二甲氧基-嘧啶-2-基-氧基)-苯基]-3-甲基-4-三氟甲基-3,6-二氢-2,6-二氧代-1(2H)-嘧啶,熔点为186℃。
式(VIII)起始物:
实施例(VIII-1)
首先使2.0g(7.0mmol)的4-溴-2-氟-5-(嘧啶-2-基-氧基)-苯胺加入25ml二氯甲烷中,在室温(约20℃)下加入0.92g(8.4mmol)氯甲酸乙酯,然后加入0.67g(8.4mmol)吡啶。然后将反应混合物在室温下搅拌4小时。随后将混合物用2N盐酸稀释至初始体积的约两倍并用二氯甲烷萃取。用硫酸钠干燥有机相并过滤。水泵抽真空条件下浓缩滤液,将残余物消解于二乙醚中并通过抽滤分离得到结晶状产物。
由此获得2.2g(理论值的89%)的N-[4-溴-2-氟-5-(嘧啶-2-基-氧基)-苯基]-氨基甲酸O-乙酯,熔点为178℃。
应用实施例:
实施例A
苗前试验
溶剂:5重量份丙酮
乳化剂:1重量份烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,使1重量份活性化合物与上述量的溶剂混合,并加入上述量的乳化剂然后将浓缩液用水稀释至所需浓度。
将测试植物的种子播种在正常土壤中。约24小时后,用活性化合物制剂喷雾土壤以使每单位面积上能够施用一定量的所需活性化合物。选择喷雾液中活性化合物的浓度以使一定量的所需活性化合物以每公顷1000升水的比例施用。
三周后,与未处理对照的植物发育情况相比评价植物的伤害程度,以%伤害表示。
下列数字表示:
0%=没有效果(类似于未处理对照)
100%=全部杀死
在上述试验中,例如制备实施例2和6的化合物表现出很强的除草活性。
实施例B
苗后试验
溶剂:5重量份丙酮
乳化剂:1重量份烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂混合,并加入上述量的乳化剂然后将浓缩液用水稀释至所需浓度。
将长至5-15cm高的测试植物用活性化合物制剂喷雾以使每单位面积上能够施用一定量的所需活性化合物。选择喷雾液的浓度以使一定量的所需活性化合物以1000升水/公顷的比例施用。
三周后,与未处理对照的植物发育情况相比评价植物的伤害程度,以%伤害表示。
下列数字表示:
0%=没有效果(类似于未处理对照)
100%=全部杀死
在上述试验中,例如制备实施例2和6的化合物表现出很强的除草活性。
Claims (18)
1.通式(I)的取代的苯基尿嘧啶类
其中
Q代表O(氧),S(硫),SO或SO2,
R1代表氢,氨基,任选地被氰基-,卤素-或C1-C4-烷氧基-取代的带有1-4个碳原子的烷基或各自任选地被卤素取代的各自带有2-4个碳原子的链烯基或炔基,
R2代表氰基,羧基,氨基甲酰基,硫代氨基甲酰基或各自任选地被氰基-,卤素-或C1-C4-烷氧基-取代的各自带有1-4个碳原子的烷基或烷氧基羰基,
R3代表氢,卤素或任选地被卤素取代的带有1-4个碳原子的烷基,
R4代表氢,硝基,氰基或卤素,
R5代表氰基,硫代氨基甲酰基,溴或各自任选地被卤素取代的各自带有1-4个碳原子的烷基或烷氧基,以及
R6代表任选地被硝基-,羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,卤素-,C1-C4-烷基-,氰基-C1-C4-烷基-,羧基-C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-C1-C4-烷基-,C1-C4-烷氧基羰基-C1-C4-烷基-,C1-C4-烷基氨基羰基烷基-,二-(C1-C4-烷基)-氨基羰基烷基-,C1-C4-烷氧基-,氰基-C1-C4-烷氧基-,C1-C4-卤代烷氧基-,C1-C4-烷氧基-C1-C4-烷氧基-,羧基-C1-C4-烷氧基-,C1-C4-烷氧基-羰基-C1-C4-烷氧基-,C1-C4-烷基氨基羰基-C1-C4-烷氧基-,二-(C1-C4-烷基)-氨基羰基-C1-C4-烷氧基-,C1-C4-烷氧基-羰基-,C2-C4-链烯基氧基-,C2-C4-炔氧基-,C1-C4-烷硫基-,C1-C4-卤代烷硫基-,C1-C4-烷基亚磺酰基-,C1-C4-卤代烷基亚磺酰基-,C1-C4-烷基磺酰基-,C1-C4-卤代烷基磺酰基-,C1-C4-烷基-羰基-氨基-,C1-C4-烷氧基-羰基-氨基-或C1-C4-烷基-磺酰基-氨基-取代的含氮杂环基,上述杂环基选自吡咯基,吡唑基,咪唑基,三唑基,三唑啉基,吡啶基,吡嗪基,哒嗪基,嘧啶基,三嗪基,苯并噁唑基,苯并噻唑基,喹啉基,喹唑啉基,喹喔啉基,
-包括通式(I)化合物的所有可能的互变异构体以及通式(I)化合物可能的盐和酸或碱加成化合物。
2.权利要求1的化合物,其特征在于
Q代表O(氧),S(硫)或SO2,
R1代表氢,氨基,各自任选地被氰基-,氟-,氯-,甲氧基-或乙氧基-取代的甲基,乙基,正-或异丙基,或各自任选地被氟-和/或氯-取代的丙烯基或丙炔基,
R2代表氰基,羧基,氨基甲酰基,硫代氨基甲酰基或各自任选地被氰基-,氟-,氯-,甲氧基-或乙氧基-取代的甲基,乙基,正或异丙基,甲氧基羰基,乙氧基羰基,正或异丙氧基羰基,
R3代表氢,氟,氯,溴或各自任选地被氟-和/或氯-取代的甲基,乙基,正或异丙基,
R4代表氢,氰基,氟,氯或溴,
R5代表氰基,硫代氨基甲酰基,溴或各自任选地被氟-和/或氯-取代的甲基,乙基,甲氧基或乙氧基,
R6代表各自任选地被硝基-,羟基-,氨基-,氰基-,羧基-,氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正或异丙基-,正-,异-,仲或叔丁基-,氯甲基-,氟甲基-,二氯甲基-,二氟甲基-,三氯甲基-,三氟甲基-,氯二氟甲基-,氟二氯甲基-,氯乙基-,氟乙基-,二氯乙基-,二氟乙基-,氯氟乙基-,三氯乙基-,三氟乙基-,氯二氟乙基-,氟二氯乙基-,四氟乙基-,氯三氟乙基-,五氟乙基-,氯正丙基-,氟正丙基-,氯异丙基-,氟异丙基-,二氯丙基-,二氟丙基-,三氯丙基-,三氟丙基-,氰甲基-,氰乙基-,氰丙基-,羧甲基-,羧乙基-,羧丙基-,甲氧基甲基-,乙氧基甲基-,丙氧基甲基-,甲氧基乙基-,乙氧基乙基-,甲氧基羰基甲基-,乙氧基羰基甲基-,正或异丙氧基羰基甲基-,甲基氨基羰基甲基-,乙基氨基羰基甲基-,二甲基氨基羰基甲基-,甲氧基羰基乙基-,乙氧基羰基乙基-,正或异丙氧基羰基乙基-,甲氧基-,乙氧基-,正或异丙氧基-,正-,异-,仲或叔丁氧基-,二氟甲氧基-,三氟甲氧基-,氯二氟甲氧基-,羧基甲氧基-,羧基乙氧基-,甲氧基羰基甲氧基-,乙氧基羰基甲氧基-,正或异丙氧基羰基甲氧基-,甲基氨基羰基甲氧基-,乙基氨基羰基甲氧基-,二甲基氨基羰基甲氧基-,甲氧基羰基乙氧基-,乙氧基羰基乙氧基-,正或异丙氧基羰基乙氧基-,甲基氨基羰基乙氧基-,乙基氨基羰基乙氧基-,二甲基氨基羰基乙氧基-,甲氧基羰基-,乙氧基羰基-,正或异丙氧基羰基-,丙烯氧基-,丁烯氧基-,丙炔氧基-,丁炔氧基-,甲硫基-,乙硫基-,正或异丙硫基-,正-,异-,仲或叔丁硫基-,二氟甲硫基-,三氟甲硫基-,氯二氟甲硫基-,甲基亚磺酰基-,乙基亚磺酰基-,正或异丙基亚磺酰基-,三氟甲基亚磺酰基-,甲基磺酰基-,乙基磺酰基-,正或异丙基磺酰基-,三氟甲基磺酰基-,乙酰基氨基-,丙酰基氨基-,正或异丁酰基氨基-,甲氧基羰基氨基-,乙氧基羰基氨基-,正或异丙氧基羰基氨基-,甲基磺酰基氨基-,乙基磺酰基氨基-,正或异丙基磺酰基氨基-取代的含氮杂环基,上述杂环基选自吡咯基,吡唑基,咪唑基,三唑基,三唑啉基,吡啶基,吡嗪基,哒嗪基,嘧啶基,三嗪基,苯并噁唑基,苯并噻唑基,喹啉基,喹唑啉基,喹喔啉基。
3.权利要求1或2的化合物,其特征在于
Q代表O(氧)或S(硫),
R1代表氢,氨基或代表各自任选地被氟-,氯-,甲氧基-或乙氧基-取代的甲基或乙基,
R2代表氰基,羧基,氨基甲酰基或各自任选地被氟-和/或氯-取代的甲基,乙基,甲氧基羰基或乙氧基羰基,
R3代表氢,氟,氯,溴或各自任选地被氟-和/或氯-取代的甲基或乙基,
R4代表氢,氟或氯,
R5代表氰基,硫代氨基甲酰基,溴或三氟甲基,以及
R6代表各自任选地被硝基-,羟基-,氨基-,氰基-,羧基-,氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正或异丙基-,正-,异-,仲或叔丁基-,二氯甲基-,二氟甲基-,三氯甲基-,三氟甲基-,氯二氟甲基-,氟二氯甲基-,甲氧基-,乙氧基-,正或异丙氧基-,正-,异-,仲或叔丁氧基-,二氟甲氧基-,三氟甲氧基-,氯二氟甲氧基-,羧基甲氧基-,羧基乙氧基-,甲氧基羰基甲氧基-,乙氧基羰基甲氧基-,正或异丙氧基羰基甲氧基-,甲氧基羰基乙氧基-,乙氧基羰基乙氧基-,正或异丙氧基羰基乙氧基-,甲氧基羰基-,乙氧基羰基-,丙烯氧基-,丁烯氧基-,丙炔氧基-,丁炔氧基-,甲硫基-,乙硫基-,正或异丙硫基-,正-,异-,仲或叔丁硫基-,二氟甲硫基-,三氟甲硫基-,氯二氟甲硫基-,甲基亚磺酰基-,乙基亚磺酰基-,正或异丙基亚磺酰基-,三氟甲基亚磺酰基-,甲基磺酰基-,乙基磺酰基-,正或异丙基磺酰基-,三氟甲基磺酰基-,乙酰基氨基-,丙酰基氨基-,正或异丁酰基氨基-,甲氧基羰基氨基-,乙氧基羰基氨基-,正或异丙氧基羰基氨基-,甲基磺酰基氨基-,乙基磺酰基氨基-,正或异丙基磺酰基氨基-取代的含氮杂环基,上述杂环基选自吡咯基,吡唑基,咪唑基,三唑基,三唑啉基,吡啶基,吡嗪基,哒嗪基,嘧啶基,三嗪基,苯并噁唑基,苯并噻唑基,喹啉基,喹唑啉基,喹喔啉基。
4.权利要求1-3中任一项的化合物,其特征在于
R1代表氢,氨基,甲基或乙基,
R2代表氰基或三氟甲基,
R3代表氢,氯或甲基,
R5代表氰基,硫代氨基甲酰基或溴,以及
R6代表各自任选地被羟基-,氨基-,氰基-,羧基-,氨基甲酰基-,氟-,氯-,溴-,甲基-,乙基-,正或异丙基-,正-,异-,仲或叔丁基-,二氯甲基-,二氟甲基-,三氯甲基-,三氟甲基-,氯二氟甲基-,氟二氯甲基-,甲氧基-,乙氧基-,正或异丙氧基-,二氟甲氧基-,三氟甲氧基-,氯二氟甲氧基-,羧基甲氧基-,羧基乙氧基-,甲氧基羰基甲氧基-,乙氧基羰基甲氧基-,正或异丙氧基羰基甲氧基-,甲氧基羰基乙氧基-,乙氧基羰基乙氧基-,正或异丙氧基羰基乙氧基-,甲氧基羰基-,乙氧基羰基-,丙烯氧基-,丁烯氧基-,丙炔氧基-,丁炔氧基-,甲硫基-,乙硫基-,正或异丙硫基-,二氟甲硫基-,三氟甲硫基-,氯二氟甲硫基-,甲基亚磺酰基-,乙基亚磺酰基-,正或异丙基亚磺酰基-,三氟甲基亚磺酰基-,甲基磺酰基-,乙基磺酰基-,正或异丙基磺酰基-,三氟甲基磺酰基-,乙酰基氨基-,丙酰基氨基-,正或异丁酰基氨基-,甲氧基羰基氨基-,乙氧基羰基氨基-,正或异丙氧基羰基氨基-,甲基磺酰基氨基-,乙基磺酰基氨基-,正或异丙基磺酰基氨基-取代的吡唑基,吡啶基,嘧啶基,三嗪基或苯并噁唑基。
5.权利要求1-4中任-项的化合物,其特征在于
R1代表氢,氨基或甲基,
R2代表三氟甲基,
R5代表氰基或溴,以及
R6代表各自任选地被羟基-,氨基-,氰基-,氟-,氯-,甲基-,乙基-,三氯甲基-,甲氧基-或乙氧基-取代的吡唑基,吡啶基,嘧啶基或苯并噁唑基。
6.权利要求1-5中任一项的化合物,其特征在于
Q代表O(氧)。
7.权利要求1-6中任一项化合物的制备方法,其特征在于
(a)如适合在反应助剂存在下以及如适合在稀释剂存在下,
其中
Q,R1,R2,R3,R4和R5各自如权利要求1-6中任一项所述定义
与通式(III)化合物反应制备
X1-R6 (III)
其中
R6如权利要求1-5中任一项所述定义以及
X1代表卤素或烷基磺酰基,
或
(b)如适合在反应助剂存在下以及如适合在稀释剂存在下,
使通式(IV)的卤代苯基尿嘧啶类
其中
R1,R2,R3,R4和R5各自如权利要求1-5中任一项所述定义以及
X2代表卤素,
与通式(V)化合物反应制备
M-Q-R6 (V)
其中
Q和R6各自如权利要求1-6中任一项所述定义以及
M代表氢或等价金属,
或
(c)如适合在反应助剂存在下以及如适合在稀释剂存在下,
使通式(VI)的氨基链烯酸酯
其中
R1,R2和R3各自如权利要求1-5中任一项所述定义以及
R代表烷基,芳基或芳烷基,
与通式(VII)的取代的异氰酸苯酯反应制备
其中
Q,R4,R5和R6各自如权利要求1-6中任一项所述定义
或与通式(VIII)的取代的苯基氨基甲酸酯类(苯基氨基甲酸酯)反应制备
其中
Q,R4,R5和R6各自如权利要求1-6中任一项所述定义以及
R代表烷基,芳基或芳烷基,
或
(d)在水存在下以及如适合在有机溶剂存在下,
其中
Q,R4,R5和R6各自如权利要求1-6中任一项所述定义以及
R′代表烷基
或
(e)如适合在反应助剂存在下以及如适合在稀释剂存在下,
其中
Q,R2,R3,R4,R5和R6各自如权利要求1-6中任一项所述定义
与1-氨基氧基-2,4-二硝基-苯或2-氨基氧基磺酰基-1,3,5-三甲基苯或与通式(X)的烷基化试剂反应进行制备
X3-A1 (X)
其中
A1代表任选地被氰基-,卤素-或C1-C4-烷氧基-取代的带有1-4个碳原子的烷基或各自任选的卤素取代的各自带有2-4个碳原子的链烯基或炔基,以及
X3代表卤素或基团-O-SO2-O-A1,
以及如适合随后以常规方式进行取代基定义范围内的亲电子或亲核反应和/或氧化或还原反应。
8.式(VII)化合物
其中
Q,R4,R5和R6各自如权利要求1-6中任一项所述定义。
10.通式(VIII)化合物
其中
Q,R4,R5,R6和R各自如权利要求1-7中任一项所述定义。
11.权利要求10化合物的制备方法,其特征在于
如适合存在酸性接受体,例如吡啶,以及如适合存在稀释剂,例如二氯甲烷,并在-20℃至+100℃的条件下
使通式(XI)的苯胺衍生物
其中
Q,R4,R5和R6各自如权利要求1-6中任一项所述定义,
与通式(XIII)的氯羰基化合物反应制备
RO-CO-Cl (XII)
其中
R代表烷基,芳基和芳烷基。
13.权利要求12化合物的制备方法,其特征在于
其中
Q,R4和Y各自如权利要求1-6和12中任一项所述定义
与通式(III)化合物反应
X1-R6 (III)
其中
R6和X1各自如权利要求1-5和7中任一项所述定义,
如适合存在酸性接受体,例如氢氧化钾,碳酸钾或吡啶,以及如适合存在稀释剂,并在0℃至200℃条件下进行反应
或
其中
R4,X2和Y各自如权利要求1-5,7和12中任一项所述定义
与通式(V)化合物反应
M-Q-R6 (V)
其中
M,Q和R6各自如权利要求1-7中任一项所述定义,
如适合存在酸性接受体以及如适合存在稀释剂,并在0℃至200℃条件下进行反应。
17.除草组合物,其特征在于该组合物包含至少一种权利要求1-6中任一项的化合物和常规填充剂。
18.至少一种权利要求1-6中任一项的化合物或权利要求17的组合物防治不需要植物的用途。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10016893.0 | 2000-04-05 | ||
DE10016893A DE10016893A1 (de) | 2000-04-05 | 2000-04-05 | Substituierte Phenyluracile |
Publications (1)
Publication Number | Publication Date |
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CN1420873A true CN1420873A (zh) | 2003-05-28 |
Family
ID=7637651
Family Applications (1)
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CN01807438A Pending CN1420873A (zh) | 2000-04-05 | 2001-03-23 | 取代的苯基尿嘧啶类 |
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US (2) | US6649760B2 (zh) |
EP (1) | EP1272478A1 (zh) |
JP (1) | JP2003530386A (zh) |
KR (1) | KR20030011793A (zh) |
CN (1) | CN1420873A (zh) |
AR (1) | AR028302A1 (zh) |
AU (1) | AU2001254731A1 (zh) |
BR (1) | BR0109784A (zh) |
CA (1) | CA2404759A1 (zh) |
DE (1) | DE10016893A1 (zh) |
MX (1) | MXPA02009835A (zh) |
PL (1) | PL358119A1 (zh) |
RU (1) | RU2002129562A (zh) |
WO (1) | WO2001077084A1 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107001288A (zh) * | 2014-09-12 | 2017-08-01 | 拜耳作物科学股份公司 | 作为害虫防治剂的具有c‑c‑连接的尿嘧啶的芳基硫醚和芳基亚砜衍生物 |
CN109311842A (zh) * | 2016-05-24 | 2019-02-05 | 巴斯夫欧洲公司 | 除草的尿嘧啶吡啶类 |
WO2020057391A1 (zh) * | 2018-09-20 | 2020-03-26 | 周银平 | 哒嗪胺类化合物的制备及其应用 |
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DE19955662B4 (de) * | 1999-11-19 | 2011-03-31 | Arysta LifeScience North America, | Herbizide auf Basis von Carbamoyltriazolinon |
BR0117032A (pt) * | 2001-05-31 | 2004-04-20 | Sumitomo Chemical Co | Reguladores de crescimento de planta para coleta de algodão |
KR100846649B1 (ko) * | 2001-08-02 | 2008-07-16 | 스미또모 가가꾸 가부시끼가이샤 | 피리딘 화합물의 제조 방법 |
JP4214707B2 (ja) * | 2002-03-27 | 2009-01-28 | 住友化学株式会社 | ピリジン化合物の製造法 |
DE10223914A1 (de) * | 2002-05-29 | 2003-12-11 | Bayer Cropscience Ag | Substituierte Phenyluracile |
ITMI20022758A1 (it) * | 2002-12-23 | 2004-06-24 | Isagro Ricerca Srl | Nuovi uracili ad attivita' erbicida. |
US20100016396A1 (en) * | 2007-01-29 | 2010-01-21 | Hiroshi Imoto | Pyrazole compound |
EP2343284B1 (en) | 2008-10-02 | 2014-12-03 | Korea Research Institute Of Chemical Technology | Uracil-based compounds, and herbicides comprising same |
WO2011137088A1 (en) * | 2010-04-27 | 2011-11-03 | E. I. Du Pont De Nemours And Company | Herbicidal uracils |
EA027605B1 (ru) * | 2011-12-06 | 2017-08-31 | Итогуми Констракшн Ко., Лтд. | Солнечная энергетическая система и способ установки солнечной панели |
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DE3275720D1 (de) | 1981-11-10 | 1987-04-23 | Ciba Geigy Ag | Phenylbenzoyl ureas as pesticides |
US5416102A (en) | 1981-11-10 | 1995-05-16 | Ciba-Geigy Corporation | Method of preventing the reinfestation of dogs and cats by fleas |
US4677117A (en) | 1982-06-28 | 1987-06-30 | Roussel Uclaf | Stabilized pesticidal compositions |
DE3337828A1 (de) | 1982-10-21 | 1984-04-26 | Ciba-Geigy Ag, Basel | Benzoylphenylthioharnstoffe |
DK366887A (da) | 1986-07-31 | 1988-05-13 | Hoffmann La Roche | Pyrimidinderivater |
US5110870A (en) * | 1989-01-06 | 1992-05-05 | Mitsubishi Kasei Corporation | Extensible film or sheet and process for producing the same |
WO1991000278A1 (de) | 1989-06-29 | 1991-01-10 | Ciba-Geigy Ag | Heterocyclische verbindungen |
AU627906B2 (en) | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
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JP2633694B2 (ja) * | 1989-08-25 | 1997-07-23 | フジテック 株式会社 | 人数検出装置 |
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JP3089621B2 (ja) | 1990-12-17 | 2000-09-18 | 日産化学工業株式会社 | ウラシル誘導体 |
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US5681794A (en) | 1993-08-18 | 1997-10-28 | Bayer Aktiengesellschaft | N-cyanoaryl-nitrogen heterocycles |
EP0648749B1 (de) | 1993-08-18 | 1997-12-10 | Bayer Ag | N-Cyanoaryl-Stickstoffheterocyclen |
DE19604229A1 (de) | 1995-02-09 | 1996-08-14 | Ciba Geigy Ag | Neue Herbizide |
HUP9802196A3 (en) | 1995-06-29 | 1999-03-01 | Bayer Agrochem Kk | Substituted cyanophenyl uracil derivatives, preparation and use thereof, insecticide and herbicide compositions containing these compounds as active ingredients |
BR9808334A (pt) | 1997-03-14 | 2000-05-16 | Isk Americas Inc | éteres diarìlicos, processos para sua preparação e composições herbicidas e dessecantes contendo os mesmos |
DE19722031A1 (de) | 1997-05-27 | 1998-12-03 | Bayer Ag | Substituierte Iminoalkoxy-phenyluracile |
CN1680274A (zh) * | 1997-10-27 | 2005-10-12 | Isk美国有限公司 | 取代的苯化合物、它们的制备方法和含它们的除草剂和脱叶剂组合物 |
BR9911978A (pt) * | 1998-07-09 | 2001-03-27 | Bayer Ag | Feniluracilas substituìdas |
US6121201A (en) | 1998-09-11 | 2000-09-19 | Ishihara Sangyo Kaisha, Ltd. | Diaryl ethers and processes for their preparation and herbicidal and desiccant compositions containing them |
IL167957A (en) | 2000-02-04 | 2009-07-20 | Sumitomo Chemical Co | Hydroxypyridine compounds |
-
2000
- 2000-04-05 DE DE10016893A patent/DE10016893A1/de not_active Withdrawn
-
2001
- 2001-03-23 US US10/019,842 patent/US6649760B2/en not_active Expired - Fee Related
- 2001-03-23 CA CA002404759A patent/CA2404759A1/en not_active Abandoned
- 2001-03-23 RU RU2002129562/04A patent/RU2002129562A/ru not_active Application Discontinuation
- 2001-03-23 WO PCT/EP2001/003332 patent/WO2001077084A1/de not_active Application Discontinuation
- 2001-03-23 AU AU2001254731A patent/AU2001254731A1/en not_active Abandoned
- 2001-03-23 JP JP2001575559A patent/JP2003530386A/ja active Pending
- 2001-03-23 BR BR0109784-9A patent/BR0109784A/pt not_active IP Right Cessation
- 2001-03-23 PL PL01358119A patent/PL358119A1/xx not_active Application Discontinuation
- 2001-03-23 CN CN01807438A patent/CN1420873A/zh active Pending
- 2001-03-23 KR KR1020027011945A patent/KR20030011793A/ko not_active Application Discontinuation
- 2001-03-23 EP EP01927790A patent/EP1272478A1/de not_active Withdrawn
- 2001-03-23 MX MXPA02009835A patent/MXPA02009835A/es unknown
- 2001-03-28 AR ARP010101475A patent/AR028302A1/es not_active Application Discontinuation
-
2003
- 2003-07-29 US US10/629,450 patent/US20040023805A1/en not_active Abandoned
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107001288A (zh) * | 2014-09-12 | 2017-08-01 | 拜耳作物科学股份公司 | 作为害虫防治剂的具有c‑c‑连接的尿嘧啶的芳基硫醚和芳基亚砜衍生物 |
CN109311842A (zh) * | 2016-05-24 | 2019-02-05 | 巴斯夫欧洲公司 | 除草的尿嘧啶吡啶类 |
CN109311842B (zh) * | 2016-05-24 | 2022-03-25 | 巴斯夫欧洲公司 | 除草的尿嘧啶吡啶类 |
WO2020057391A1 (zh) * | 2018-09-20 | 2020-03-26 | 周银平 | 哒嗪胺类化合物的制备及其应用 |
Also Published As
Publication number | Publication date |
---|---|
MXPA02009835A (es) | 2003-05-27 |
CA2404759A1 (en) | 2002-10-02 |
BR0109784A (pt) | 2003-01-21 |
KR20030011793A (ko) | 2003-02-11 |
WO2001077084A1 (de) | 2001-10-18 |
US20020173425A1 (en) | 2002-11-21 |
US20040023805A1 (en) | 2004-02-05 |
AU2001254731A1 (en) | 2001-10-23 |
RU2002129562A (ru) | 2004-03-10 |
DE10016893A1 (de) | 2001-10-18 |
PL358119A1 (en) | 2004-08-09 |
JP2003530386A (ja) | 2003-10-14 |
AR028302A1 (es) | 2003-05-07 |
US6649760B2 (en) | 2003-11-18 |
EP1272478A1 (de) | 2003-01-08 |
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