CN102906096A - 具有除草作用的吡啶类 - Google Patents
具有除草作用的吡啶类 Download PDFInfo
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- CN102906096A CN102906096A CN2011800246379A CN201180024637A CN102906096A CN 102906096 A CN102906096 A CN 102906096A CN 2011800246379 A CN2011800246379 A CN 2011800246379A CN 201180024637 A CN201180024637 A CN 201180024637A CN 102906096 A CN102906096 A CN 102906096A
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- Prior art keywords
- alkyl
- compound
- group
- formula
- alkoxy
- 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.)
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- 150000003222 pyridines Chemical class 0.000 title claims abstract description 12
- 230000002363 herbicidal effect Effects 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 251
- 239000000203 mixture Substances 0.000 claims abstract description 75
- 150000003839 salts Chemical class 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 35
- -1 N-oxide compound Chemical class 0.000 claims description 157
- 229910052760 oxygen Inorganic materials 0.000 claims description 51
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 150000003851 azoles Chemical class 0.000 claims description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 229910004013 NO 2 Inorganic materials 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical class 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 239000012752 auxiliary agent Substances 0.000 claims description 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 239000011814 protection agent Substances 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
- 150000003217 pyrazoles Chemical class 0.000 claims description 3
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 150000003053 piperidines Chemical class 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 10
- 239000004009 herbicide Substances 0.000 abstract description 9
- 239000000543 intermediate Substances 0.000 abstract description 3
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 description 98
- 229940126062 Compound A Drugs 0.000 description 62
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 62
- 241000196324 Embryophyta Species 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 229910052727 yttrium Inorganic materials 0.000 description 30
- 230000000694 effects Effects 0.000 description 29
- 150000003254 radicals Chemical class 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000003513 alkali Substances 0.000 description 27
- 239000000460 chlorine Substances 0.000 description 27
- 244000025254 Cannabis sativa Species 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 238000009333 weeding Methods 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 239000011737 fluorine Substances 0.000 description 19
- 108090000623 proteins and genes Proteins 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 16
- 239000000049 pigment Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 240000008042 Zea mays Species 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- XFTWUNOVBCHBJR-UHFFFAOYSA-N Aspergillomarasmine A Chemical compound OC(=O)C(N)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O XFTWUNOVBCHBJR-UHFFFAOYSA-N 0.000 description 13
- 101000963974 Hydrophis stokesii Alpha-elapitoxin-Ast2b Proteins 0.000 description 13
- 101000964025 Naja naja Long neurotoxin 3 Proteins 0.000 description 13
- 229910001413 alkali metal ion Inorganic materials 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 13
- 239000003112 inhibitor Substances 0.000 description 13
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 235000005822 corn Nutrition 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 11
- 241000219146 Gossypium Species 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 102000004169 proteins and genes Human genes 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 239000003053 toxin Substances 0.000 description 10
- 231100000765 toxin Toxicity 0.000 description 10
- 108700012359 toxins Proteins 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 244000061456 Solanum tuberosum Species 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 235000002595 Solanum tuberosum Nutrition 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
- 239000000080 wetting agent Substances 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- 239000005562 Glyphosate Substances 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- QLULGSLAHXLKSR-UHFFFAOYSA-N azane;phosphane Chemical compound N.P QLULGSLAHXLKSR-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000009331 sowing Methods 0.000 description 7
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 7
- 229940124530 sulfonamide Drugs 0.000 description 7
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
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- 244000068988 Glycine max Species 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
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- HQRPHMAXFVUBJX-UHFFFAOYSA-N lithium;carbonic acid Chemical compound [Li+].OC(O)=O HQRPHMAXFVUBJX-UHFFFAOYSA-N 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- 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 6
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- IKVXBIIHQGXQRQ-CYBMUJFWSA-N propan-2-yl (2r)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-CYBMUJFWSA-N 0.000 description 1
- IKVXBIIHQGXQRQ-UHFFFAOYSA-N propan-2-yl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical class N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 description 1
- BBKDWPHJZANJGB-UHFFFAOYSA-N quizalofop-p-tefuryl Chemical group C=1C=C(OC=2N=C3C=CC(Cl)=CC3=NC=2)C=CC=1OC(C)C(=O)OCC1CCCO1 BBKDWPHJZANJGB-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000002795 scorpion venom Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical class [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- CLHHSSXFXYAXDB-UHFFFAOYSA-M sodium;2-(naphthalen-1-ylcarbamoyl)benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 CLHHSSXFXYAXDB-UHFFFAOYSA-M 0.000 description 1
- JUNDBKFAZXZKRA-MAFYXNADSA-M sodium;2-[(e)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylate Chemical compound [Na+].N=1C=CC=C(C([O-])=O)C=1C(/C)=N/NC(=O)NC1=CC(F)=CC(F)=C1 JUNDBKFAZXZKRA-MAFYXNADSA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000002708 spider venom Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 230000037359 steroid metabolism Effects 0.000 description 1
- 108010076424 stilbene synthase Proteins 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 235000018322 upland cotton Nutrition 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 150000004669 very long chain fatty acids Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002578 wasp venom Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Abstract
公开了式(I)的取代吡啶,其中各变量如说明书所定义,制备式(I)化合物及其N-氧化物、其可农用盐的方法和中间体,包含它们的组合物及其作为除草剂的用途,还公开了防止不希望的植物生长的方法。
Description
本发明涉及式I的取代吡啶或其N-氧化物或可农用盐:
其中各变量具有下列含义:
R为O-RA、S(O)n-RA或O-S(O)n-RA;
RA为氢、C1-C4烷基、Z-C3-C6环烷基、C1-C4卤代烷基、C2-C6链烯基、Z-C3-C6环烯基、C2-C6炔基、Z-(三-C1-C4烷基)甲硅烷基、Z-C(=O)-Ra、Z-NRi-C(O)-NRiRii、Z-P(=O)(Ra)2、NRiRii、3-7员单环或9-10员双环饱和、不饱和或芳族杂环,该杂环含有1、2、3或4个选自O、N和S的杂原子并且可以部分或完全被基团Ra和/或Rb取代,
Ra为氢、OH、C1-C8烷基、C1-C4卤代烷基、Z-C3-C6环烷基、C2-C8链烯基、Z-C5-C6环烯基、C2-C8炔基、Z-C1-C6烷氧基、Z-C1-C4卤代烷氧基、Z-C3-C8链烯氧基、Z-C3-C8炔氧基、NRiRii、C1-C6烷基磺酰基、Z-(三-C1-C4烷基)甲硅烷基、Z-苯基、Z-苯氧基、Z-苯基氨基或含有1、2、3或4个选自O、N和S的杂原子的5-6员单环或9-10员双环杂环,其中环状基团未被取代或者被1、2、3或4个基团Rb取代;
Ri、Rii相互独立地为氢、C1-C8烷基、C1-C4卤代烷基、C3-C8链烯基、C3-C8炔基、Z-C3-C6环烷基、Z-C1-C8烷氧基、Z-C1-C8卤代烷氧基、Z-C(=O)-Ra、Z-苯基、含有1、2、3或4个选自O、N和S的杂原子并且经由Z连接的3-7员单环或9-10员双环饱和、不饱和或芳族杂环;
Ri和Rii与它们所连接的氮原子一起还可以形成含有1、2、3或4个选自O、N和S的杂原子的5-6员单环或9-10员双环杂环;
Z为共价键或C1-C4亚烷基;
n为0、1或2;
R1为氰基、卤素、硝基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6卤代烷基、Z-C1-C6烷氧基、Z-C1-C4烷氧基-C1-C4烷氧基、Z-C1-C4烷硫基、Z-C1-C4烷硫基-C1-C4烷硫基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基、C1-C4卤代烷氧基-C1-C4烷氧基、S(O)nRbb、Z-苯氧基、Z-杂环氧基,其中杂环基为含有1、2、3或4个选自O、N和S的杂原子的5-6员单环或9-10员双环饱和、部分不饱和或芳族杂环,其中环状基团未被取代或者部分或完全被Rb取代;
Rbb为C1-C8烷基、C2-C6链烯基、C2-C6炔基、C2-C6卤代链烯基、C2-C6
卤代炔基或C1-C6卤代烷基且n为0、1或2;
A为N或C-R2;
R2为Z1-苯基、苯氧基或Z1-杂环基,其中杂环基为含有1、2、3或4个选自O、N和S的杂原子的5-6员单环或9-10员双环饱和、部分不饱和或芳族杂环,其中环状基团未被取代或者部分或完全被Rb取代;C1-C8烷基、C2-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基、C2-C8链烯基、C2-C8炔基、C2-C8卤代链烯基、C2-C8卤代炔基、C2-C6烷氧基、Z-C1-C4烷氧基-C1-C4烷氧基、Z-C1-C4卤代烷氧基-C1-C4烷氧基、C2-C6卤代烷氧基、C3-C6链烯氧基、C3-C6炔氧基、C2-C6烷硫基、C2-C6卤代烷硫基、Z-C(=O)-Ra、S(O)1-2Rbb;
Z1为共价键、C1-C4亚烷氧基、C1-C4氧亚烷基或C1-C4亚烷氧基-C1-C4亚烷基;
Rb相互独立地为Z-CN、Z-OH、Z-NO2、Z-卤素、氧代(=O)、=N-Ra、C1-C8烷基、C1-C4卤代烷基、C2-C8链烯基、C2-C8炔基、Z-C1-C8烷氧基、Z-C1-C8卤代烷氧基、Z-C3-C10环烷基、O-Z-C3-C10环烷基、Z-C(=O)-Ra、NRiRii、Z-(三-C1-C4烷基)甲硅烷基、Z-苯基和S(O)nRbb;两个基团Rb可以一起形成具有3-6个环成员且除了碳原子外还可以含有选自O、N和S的杂原子以及可以未被取代或者被其他基团Rb取代的环;
R2与相邻碳原子所连接的基团一起还可以形成除了碳原子外还可以含有1、2或3个选自O、N和S的杂原子并且可以被其他基团Rb取代的5-10员饱和或部分或完全不饱和单环或双环;
R3为氢、卤素、氰基、硝基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C4链烯基、C2-C4炔基、C2-C4链烯氧基、C2-C4炔氧基、S(O)nRbb;
R4为氢、卤素或C1-C4卤代烷基;
R5为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷氧基、C1-C4卤代烷硫基;
R6、R7相互独立地为氢、卤素或C1-C4烷基;
Y为O或S;
X为O、S或N-Rx;
Rx为氢、C1-C6烷基、C1-C4卤代烷基、C2-C6链烯基、C3-C6炔基、Z-C3-C10环烷基、C1-C6烷氧基-C1-C6烷基、C1-C6氰基烷基、Z-苯基、Z-C(=O)-Ra2或三-C1-C4烷基甲硅烷基;
Ra2为C1-C6烷基、C1-C4卤代烷基、Z-C1-C6烷氧基、Z-C1-C4卤代烷氧基或NRiRii;
其中在基团RA及其子取代基中,碳链和/或环状基团可以部分或完全被基团Rb取代。
此外,本发明涉及制备式I的吡啶及其N-氧化物、其可农用盐的方法和中间体,还涉及包含它们的活性化合物组合,包含它们的组合物及其作为除草剂,即防治有害植物的用途,还涉及一种防治不希望的植物生长的方法,包括使除草有效量的至少一种式I的吡啶化合物或I的可农用盐作用于植物、其种子和/或其生长场所。
本发明的其他实施方案可以在权利要求书、说明书和实施例中找到。应理解的是本发明主题的上述特征和下文仍要说明的那些不仅可以用于各种给定组合,而且可以在不背离本发明范围下用于其他组合。
WO2008/009908、WO2008/071918、WO2009/090401、WO2009/090402和WO2010/029311描述了除草的吡啶并吡嗪类;然而,它们在低施用率下的除草作用和/或它们与农作物的相容性仍有待改进。
本发明的目的是提供具有除草作用的化合物。尤其要提供尤其甚至在低施用率下具有强除草作用的活性化合物,其与农作物的相容性对商业应用而言是足够的。
这些和其他目的由开头所定义的式I化合物及其N-氧化物和其可农用盐实现。
本发明化合物可以类似于上述文献中所述合成途径根据有机化学的标准方法,例如根据下列合成途径制备:
可以使式II的吡啶甲酸与式III的羰基化合物反应而得到式IV化合物。在式II和III中,各变量具有对式I所给含义。基团Hal为卤原子或另一合适的亲核离去基团,如烷氧基或苯氧基。
该反应通常在-78°C至120°C,优选-20°C至50°C的温度下在惰性有机溶剂中在碱如三乙胺(参见J.Agric.and Food Chem.1994,42(4),1019-1025)、催化剂如二环己基碳二亚胺(参见Egyptian Journal ofChemistry 1994,37(3),273-282)或其他已知偶联剂存在下进行。
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类,如二氯甲烷、氯仿和氯苯,醚类,如***、二异丙醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,还有二甲亚砜、二甲基甲酰胺和二甲基乙酰胺,特别优选卤代烃类,如二氯甲烷、氯仿和氯苯。还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钙,还有碱金属碳酸氢盐,如碳酸氢钠,有机金属化合物,尤其是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基卤化镁,如甲基氯化镁,还有碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁,此外还有有机碱,例如叔胺,如三甲胺、三乙胺、三丁胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶,如可力丁、卢剔啶和4-二甲氨基吡啶,以及还有双环胺。特别优选叔胺如三甲胺、三乙胺、三丁胺、二异丙基乙基胺以及碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钙。碱通常以等摩尔量使用;然而,它们还可以以催化量、过量使用或者合适的话用作溶剂。
原料通常以等摩尔量相互反应。
式IV化合物通过引入离去基团L1而活化。合适的离去基团L1通常为提高羰基的亲电性的基团,例如O-烷基、O-芳基、卤化物、活化酯或醛(例如Weinreb酰胺),尤其是五氟苯氧基。
该反应通常在-78°C至120°C,优选-20°C至50°C的温度下在惰性有机溶剂中在碱如三乙胺(参见J.Agric.and Food Chem.1994,42(4),1019-1025)、催化剂如二环己基碳二亚胺(参见Egyptian Journal ofChemistry 1994,37(3),273-282)或其他已知偶联剂存在下进行。
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类,如二氯甲烷、氯仿和氯苯,醚类,如***、二异丙醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,还有二甲亚砜、二甲基甲酰胺和二甲基乙酰胺,特别优选二氯甲烷和甲苯。还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钙,还有碱金属碳酸氢盐,如碳酸氢钠,有机金属化合物,尤其是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基卤化镁,如甲基氯化镁,还有碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁,此外还有有机碱,例如叔胺,如三甲胺、三乙胺、三丁胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶,如可力丁、卢剔啶和4-二甲氨基吡啶,以及还有双环胺。特别优选碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾、碳酸钙、碳酸铯和碳酸铷。碱通常以催化量使用;然而,它们还可以以等摩尔量、过量使用或者合适的话用作溶剂。
原料通常以等摩尔量相互反应。
合适的试剂H-L1是醇,任选取代的酚,N,O-二烷基羟胺,尤其是五氟苯酚或N,O-二甲基羟胺。
将式V化合物环化而得到式I化合物。
该反应通常在-78°C至120°C,优选-20°C至50°C的温度下在惰性有机溶剂中在碱或路易斯酸或催化剂存在下进行[参见Silverman,Richard B.J.Am.Chem.Soc.1981,103(13),3910]。
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类,如二氯甲烷、氯仿和氯苯,醚类,如***、二异丙醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,还有二甲亚砜、二甲基甲酰胺和二甲基乙酰胺,特别优选乙腈和二甲基甲酰胺。还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾、碳酸钙、碳酸铯和碳酸铷,还有碱金属碳酸氢盐,如碳酸氢钠,有机金属化合物,尤其是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基卤化镁,如甲基氯化镁,还有碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁,此外还有有机碱,例如叔胺,如三甲胺、三乙胺、三丁胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶,如可力丁、卢剔啶和4-二甲氨基吡啶,以及还有双环胺。特别优选碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾、碳酸钙、碳酸铯和碳酸铷。
碱通常以催化量使用;然而,它们还可以以等摩尔量、过量使用或者合适的话用作溶剂。
原料通常以等摩尔量相互反应。
或者,式I化合物还可以经由反转的反应顺序得到,即,使式II化合物与化合物H-L1反应得到式VI的活化衍生物。
该反应本身在对式IV化合物与H-L1反应所述的条件下进行。
然后可以使式VI化合物与化合物III反应得到式V的衍生物。
该反应本身在对式II化合物与式III化合物反应所述的条件下进行。
式III的苯基乙酸衍生物是已知的或者可以基于文献中已知的合成途径由相应取代的苯甲酸或卤代苯制备[参见Journal of Medicinal Chemistry49(12),3563-3580(2006);Journal of Medicinal Chemistry 28(10),1533-6(1985);US 2004/077901;US 2004/068141;Chemistry-A EuropeanJournal 14(26),7969-7977(2008);Journal of Enzyme Inhibition andMedicinal Chemistry 17(3),187-196(2002)]。适当取代的苯甲酸和卤代苯例如由WO 2002/006211,WO 2009/058237,WO 98/52926,WO 96/26193,EP-A 352543,WO 98/52926,WO 97/30986,WO 98/12180已知。
反应混合物以常规方式后处理,例如与水混合,分离各相以及合适的话层析提纯粗产物。某些中间体和终产物以无色或浅褐色粘稠油形式得到,通常将它们在减压和温和升高的温度下提纯或除去挥发性组分。若中间体和终产物以固体得到,则还可以通过重结晶或浸煮进行提纯。
若各化合物I不能通过上述途径得到,则可以通过衍生其他化合物I制备它们。
然而,若合成得到异构体混合物,则通常不一定要求分离,因为在某些情况下各异构体可在为了应用的后处理过程中或在施用过程中(例如在光、酸或碱的作用下)相互转化。该类转化也可以在施用后发生,例如在植物处理的情况下在被处理的植物中或在待防治的有害植物中发生。
对本发明化合物的取代基所提到的有机结构部分是各基团成员的单独列举的集合性术语。所有烃链,如烷基、卤代烷基、链烯基、炔基以及烷氧基、卤代烷氧基、烷基氨基、二烷基氨基、N-烷基磺酰基氨基、链烯氧基、炔氧基、烷氧基氨基、烷基氨基磺酰基氨基、二烷基氨基磺酰基氨基、链烯基氨基、炔基氨基、N-链烯基-N-烷基氨基、N-炔基-N-烷基氨基、N-烷氧基-N-烷基氨基、N-链烯基-N-烷氧基氨基或N-炔基-N-烷氧基氨基中的烷基结构部分和链烯基结构部分可以是直链或支化的。
前缀Cn-Cm-表示烃单元的相应碳数。除非另有指明,卤代取代基优选带有1-5个相同或不同的卤原子,尤其是氟原子或氯原子。
含义卤素在每种情况下指氟、氯、溴或碘。
其他含义的实例是:烷基以及例如在烷氧基、烷基氨基、二烷基氨基中的烷基结构部分:具有一个或多个碳原子,例如1或2个,1-4个或1-6个碳原子的饱和直链或支化烃基,例如C1-C6烷基,如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基。在本发明的一个实施方案中,烷基表示小烷基,如C1-C4烷基。在本发明的另一实施方案中,烷基表示相对大的烷基,如C5-C6烷基。
卤代烷基:其氢原子中一些或全部被卤原子如氟、氯、溴和/或碘替代的上述烷基,例如氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、2-氟乙基、2-氯乙基、2-溴乙基、2-碘乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-(氟甲基)-2-氟乙基、1-(氯甲基)-2-氯乙基、1-(溴甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基和九氟丁基。
环烷基以及例如在环烷氧基或环烷基羰基中的环烷基结构部分:具有3个或更多个碳原子,例如3-6个碳环成员的单环饱和烃基,如环丙基、环丁基、环戊基和环己基。
链烯基以及例如在链烯氧基中的链烯基结构部分:具有2个或更多个碳原子,例如2-4个、2-6个或3-6个碳原子和在任意位置的双键的单不饱和直链或支化烃基,例如C2-C6链烯基,如乙烯基、1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基、1-乙基-2-甲基-2-丙烯基。
环烯基:具有3-6个,优选5或6个碳环成员的单环单不饱和烃基,如环戊烯-1-基、环戊烯-3-基、环己烯-1-基、环己烯-3-基、环己烯-4-基。
炔基以及例如在炔氧基、炔基氨基中的炔基结构部分:具有2个或更多个碳原子,例如2-4个、2-6个或3-6个碳原子和在任意位置的叁键的直链或支化烃基,例如C2-C6炔基,如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、3-甲基-1-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-1-戊炔基、3-甲基-4-戊炔基、4-甲基-1-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基、1-乙基-1-甲基-2-丙炔基。
烷氧基:经由氧原子连接的如上所定义的烷基:例如甲氧基、乙氧基、正丙氧基、1-甲基乙氧基、丁氧基、1-甲基丙氧基、2-甲基丙氧基或1,1-二甲基乙氧基、戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、2,2-二甲基丙氧基、1-乙基丙氧基、己氧基、1-甲基戊氧基、2-甲基戊氧基、3-甲基戊氧基、4-甲基戊氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,2-二甲基丁氧基、2,3-二甲基丁氧基、3,3-二甲基丁氧基、1-乙基丁氧基、2-乙基丁氧基、1,1,2-三甲基丙氧基、1,2,2-三甲基丙氧基、1-乙基-1-甲基丙氧基或1-乙基-2-甲基丙氧基。
含有1、2、3或4个选自O、N和S的杂原子且可以经由碳或氮连接的3-7员单环或9或10员双环饱和、不饱和或芳族杂环。其中优选5或6员杂环。
经由氮或碳连接的饱和或不饱和杂环基团,如哒嗪-3-基、哒嗪-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、吡嗪-2-基、异唑啉-3-基、异唑啉-4-基、异唑啉-5-基、异噻唑-3-基、异噻唑-4-基、异噻唑-5-基、咪唑-1-基、咪唑-2-基、咪唑-4-基、唑-2-基、唑啉-4-基、噻唑啉-2-基和吗啉基。
经由氮或碳连接的杂芳族基团,如吡唑-3-基、2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、吡唑-1-基、吡唑-3-基、吡唑-4-基、异唑-3-基、异唑-4-基、异唑-5-基、咪唑-5-基、唑-2-基、唑-4-基、唑-5-基、噻唑-2-基、噻唑-4-基、噻唑-5-基、吡啶-2-基、吡啶-3-基、吡啶-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、哒嗪-4-基、吡嗪-2-基、[1H]-四唑-5-基和[2H]-四唑-5-基。
取决于取代方式,式I化合物可以含有一个或多个其他手性中心。因此,本发明化合物可以作为纯对映体或非对映体或对映体或非对映体混合物存在。本发明提供了纯对映体或非对映体及其混合物。
式I化合物还可以以其N-氧化物和/或其可农用盐形式存在,盐的类型通常并不重要。合适的盐通常是其阳离子和阴离子分别对化合物I的除草活性没有不利影响的那些阳离子的盐或那些酸的酸加成盐。
合适的阳离子尤其是碱金属的离子,优选锂、钠或钾离子,碱土金属的离子,优选钙或镁离子,以及过渡金属的离子,优选锰、铜、锌或铁离子。可以使用的其他阳离子是其中需要的话1-4个氢原子可以被C1-C4烷基、羟基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、羟基-C1-C4烷氧基-C1-C4烷基、苯基或苄基替代的铵,优选铵、二甲基铵、二异丙基铵、四甲基铵、四丁基铵、2-(2-羟基乙-1-氧基)乙-1-基铵、二(2-羟基乙-1-基)铵、三甲基苄基铵。另一合适的铵阳离子是通过烷基化或芳基化季化的式I的吡啶氮原子。合适的还有离子,锍离子,优选三(C1-C4烷基)锍,或氧化锍离子,优选三(C1-C4烷基)氧化锍。
合适酸加成盐的阴离子主要是氯离子、溴离子、氟离子、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根以及C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根、丁酸根或三氟乙酸根。
对于各变量,中间体的特别优选实施方案对应于式I的基团的那些。
在特殊实施方案中,式I化合物的各变量具有下列含义,这些含义本身和相互组合为式I化合物的特殊实施方案:
在式I化合物的一个优选实施方案中,R为O-RA,其中RA为H,C3-C8链烯基,C3-C8卤代链烯基,C3-C8炔基,C3-C8卤代炔基,C1-C6烷基羰基如C(O)CH3、C(O)CH2CH3、C(O)CH(CH3)2或C(O)C(CH3)3,C1-C6环烷基羰基,如环丙基羰基、环戊基羰基或环己基羰基,C2-C6链烯基羰基,如C(O)CH=CH2或C(O)CH2CH=CH2,任选取代的苯甲酰基,如C(O)C6H5、C(O)[2-CH3-C6H4]、C(O)[4-CH3-C6H4]、C(O)[2-F-C6H4]、C(O)[4-F-C6H4],或经由羰基连接的任选取代的杂芳基,如吡啶基。特别优选RA为H、C3-C4链烯基、C3-C4炔基或C1-C6烷基羰基。尤其优选RA选自H、CH2CH=CH2、CH2C≡CH、CH3、C(O)CH3、C(O)CH2CH3、C(O)CH(CH3)2、C(O)C(CH3)3、C(O)-c-C3H5、C(O)-C6H5、C(O)-CH2C6H5、C(O)CH2Cl 、C(O)CF3、C(O)CH2OCH3、C(O)N(CH3)2和C(O)OCH2CH3。
在式I化合物的另一优选实施方案中,R为OS(O)n-RA,其中n优选为0或2,尤其是2,例如OS(O)2-CH3、OS(O)2-C2H5、OS(O)2-C3H7、OS(O)2-C6H5或OS(O)2-(4-CH3-C6H4)。
在另一优选实施方案中,R为O-S(O)n-NRiRii,尤其具有下文作为优选提到的基团NRiRii。
Ri和Rii优选为C1-C8烷基、C1-C4卤代烷基、Z-C3-C6环烷基、Z-C1-C8烷氧基、Z-C1-C8卤代烷氧基、Z-苯基、Z-C(=O)-Ra或Z-杂芳基。这里优选CH3、C2H5、正丙基、CH(CH3)2、丁基、2-氯乙基、环戊基、环己基、2-乙氧基甲基、2-氯乙氧基、苯基、嘧啶类或三嗪类,这些环未被取代或者被取代。优选的取代基是C1-C4烷基羰基或C1-C4卤代烷基羰基,尤其是C(=O)-CH3、C(=O)-C2H5、C(=O)-C3H7、C(=O)-CH(CH3)2、丁基羰基和C(=O)-CH2Cl。基团NRiRii的特别优选方面是N(二-C1-C4烷基),尤其是N(CH3)-C1-C4烷基,如N(CH3)2、N(CH3)CH2CH3、N(CH3)C3H7和N(CH3)CH(CH3)2。
NRiRii的其他特别优选方面是NH-芳基,其中芳基优选为被1-3个选自如下的相同或不同基团取代的苯基,尤其在2和6位取代:卤素、CH3、卤代-C1-C2烷基、卤代-C1-C2烷氧基和羧基,如2-Cl,6-COOH-C6H3、2,6-Cl2-C6H3、2,6-F2-C6H3、2,6-Cl23-C6H2、2-CF3,6-CH2CHF2-C6H3、2-CF3,6-OCF3-C6H3和2-CF3,6-CH2CHF2-C6H3。
在本发明的另一优选实施方案中,RA为任选被如上所定义的Rb取代的5或6员杂环,其优选具有1、2、3或4个N或1个O或1个S原子和合适的话1或2个N原子作为环成员且未被取代或者可以具有1或2个选自Rb的取代基。优选经由氮连接的饱和或不饱和基团,如杂芳族基团:哒嗪-3-基、哒嗪-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、吡嗪-2-基、2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、吡唑-1-基、吡唑-3-基、吡唑-4-基、异唑-3-基、异唑-4-基、异唑-5-基、异噻唑-3-基、异噻唑-4-基、异噻唑-5-基、咪唑-1-基、咪唑-2-基、咪唑-4-基、唑-2-基、唑-4-基、唑-5-基、噻唑-2-基、噻唑-4-基和噻唑-5-基。
在另一方面,RA为经由碳连接的杂芳族基团,如吡唑-3-基、咪唑-5-基、唑-2-基、噻唑-2-基、噻唑-4-基、噻唑-5-基、吡啶-2-基、吡啶-3-基、吡啶-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、哒嗪-4-基、吡嗪-2-基、[1H]-四唑-5-基和[2H]-四唑-5-基,其中此处以示例方式提到的杂环各自可以具有1或2个选自Rb的取代基。优选的基团Rb此时尤其为F、Cl、CN、NO2、CH3、C2H5、OCH3、OC2H5、OCHF2、OCF3和CF3。
在式I化合物的特别优选实施方案中,R选自OH、OCH2CH=CH2、OCH2C≡CH、OCH3、OC(O)CH3、OC(O)CH2CH3、OC(O)CH(CH3)2、OC(O)C(CH3)3、OC(O)-c-C3H5、OC(O)-C6H5、OC(O)-CH2C6H5、OC(O)CH2Cl、OC(O)-CF3、OC(O)-CH2OCH3、OC(O)-N(CH3)2和OC(O)-OCH2CH3。
对式I化合物优选的基团Ra选自OH、C1-C8烷基、C1-C4卤代烷基、C3-C8链烯基、C3-C8炔基、Z-C1-C6烷氧基、Z-C1-C4卤代烷氧基、Z-C3-C8链烯氧基、Z-C3-C8炔氧基和NRiRii。
对于式I化合物,基团Rb优选选自卤素、氧代(=O)、=N-Ra、C1-C4烷基、C1-C4卤代烷基、C2-C6链烯基、C2-C6炔基、Z-C1-C4卤代烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷硫基-C1-C4烷基、Z-C(=O)-Ra和S(O)nRbb,其中Rbb优选为C1-C4烷基或C1-C4卤代烷基且n为0、1或2。
特别优选Rb为选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C3-C4链烯基、C3-C4炔基和=N-C1-C4烷氧基的基团。
两个基团Rb可以一起形成优选具有3-7个环成员且除了碳原子外还可以含有选自O、N和S的杂原子以及可以未被取代或被其他基团Rb取代的环。这些取代基Rb优选选自卤素、C1-C4烷基、C1-C4烷氧基和C1-C4卤代烷基。
若存在多个基团Ra和Rb,则这类基团相互独立地选择。
在式I化合物的优选实施方案中,R1为卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基、C1-C4烷硫基-C1-C4烷硫基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C4链烯氧基、C3-C4炔氧基、C1-C4烷氧基-C1-C4烷氧基、C1-C4卤代烷氧基-C1-C4烷氧基、S(O)n-C1-C4烷基和S(O)n-C1-C4卤代烷基。特别优选R1选自F、Cl、Br、NO2、CH3、CF3、OCH3、OCF3、SCF3、SO2CH3、OCH2CH2OCH3、CH2OCH2CH2OCH3、CH2OCH2CF3。
在式I化合物的另一优选实施方案中,A为C-R2。这些化合物对应于式I.1:
其中各变量具有开头所定义的含义,优选作为优选提到的含义。
特别优选在式I.1化合物中,基团
R1为卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基或C1-C4烷基磺酰基,尤其是F、Cl、Br、NO2、CH3、CF3、OCH3、OCF3、OCHF2、SCF3、SCHF2、SO2CH3、CH2OCH2CH2OCH3;
R3为H、卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基,尤其是H、F、Cl、Br、CN、NO2、CH3、CH2CH3、CF3、CHF2、OCH3、OCF3、OCHF2、SCH3、SO2CH3或SO2CH2CH3;
R4为H或卤素,尤其是H、F或Cl。
R2优选为苯基或经由Z1连接且含有1、2、3或4个选自O、N和S的杂原子的3-7员单环或9或10员双环饱和、部分不饱和或芳族杂环,其中环状基团未被取代或者部分或完全被基团Rb取代。
在式I.1化合物的优选方面,R2为直接或经由C1-C4亚烷氧基、C1-C4氧亚烷基或C1-C4亚烷氧基-C1-C4亚烷基连接的3-7员单环或9或10员双环饱和、部分不饱和或芳族杂环,其含有1、2、3或4个选自O、N和S的杂原子并且可以如开头所定义那样被取代。
基团R2的优选方面涉及5或6员饱和或部分不饱和杂环,如异唑啉、四唑酮、1,2-二氢四唑酮、1,4-二氢四唑酮、四氢呋喃、二氧戊环、哌啶、吗啉和哌嗪。特别优选3-异唑啉、5-异唑啉、1-四唑酮、2-四唑酮、[1,3]二氧戊环-2和N-吗啉。尤其优选未被取代或被5-CH3、5-CH2F或5-CHF2取代的4,5-二氢异唑-3;未被取代或被3-CH3、3-OCH3、3-CH2OCH3、3-CH2SCH3取代的4,5-二氢异唑-5;1-甲基-5-氧代-1,5-二氢四唑-2;4-甲基-5-氧代-4,5-二氢四唑-1和N-吗啉。
基团R2的另一优选方面涉及5或6员芳族杂环,如异唑、吡唑、噻唑、呋喃、吡啶、嘧啶和吡嗪。特别优选3-异唑、5-异唑、3-吡唑、5-吡唑、2-噻唑、2-唑、2-呋喃基。尤其优选3-异唑、5-甲基-3-异唑、5-异唑、3-甲基-5-异唑、1-甲基-1H-吡唑-3、2-甲基-2H-吡唑-3和噻唑-2。
在杂环基团R2的优选方面,基团Rb优选为C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基、C1-C4烷硫基或C1-C4烷基磺酰基。尤其优选CH3、C2H5、CH2F、CF2H、CF3、OCH3、CH2OCH3、CH2SCH3、SCH3和SO2CH3。
在优选方面,基团Z1为共价键。
在另一优选方面,基团Z1为C1-C4亚烷氧基,尤其是OCH2或OCH2CH2。
在另一优选方面,基团Z1为C1-C4氧亚烷基,尤其是CH2O或CH2CH2O。
在另一优选方面,基团Z1为C1-C4亚烷氧基-C1-C4亚烷基,尤其是OCH2OCH2或OCH2CH2OCH2。
经由Z1连接的杂环的特别优选方面包括四氢呋喃-2-基甲氧基甲基和[1,3]二氧戊环-2-基甲氧基。
在式I.1化合物的另一优选方面,R2为可以部分或完全被基团Rb取代,优选单-、二-或三取代,尤其是单取代的苯基。对该方面优选的基团Rb包括卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷氧基。特别优选卤素,如F或Cl,CH3,C2H5,OCH3,OC2H5,CHF2,CF3,OCHF2,OCF3,OCH2OCH3,OCH2CH2OCH3。尤其优选烷氧基,如OCH3或OC2H5。基团Rb优选位于4位。特别优选的苯基R2为基团P:
其中#表示基团R2经由其连接的键且取代基选自Rb,尤其为:
RP2为H或F;
RP3为H、F、Cl或OCH3;以及
RP4为H、F、Cl、CH3、CF3、OCH3、OCH2OCH3或OCH2CH2OCH3。
在式I.1化合物的另一优选方面,R2为选自C1-C6烷基、C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷氧基-C1-C4烷基、C2-C6链烯基、C2-C6炔基、C2-C4烷氧基、C2-C4卤代烷氧基、C3-C6链烯氧基、C3-C6炔氧基、C3-C6卤代链烯氧基、C3-C6卤代炔氧基、C1-C4烷氧羰基、S(O)2-C1-C4烷基和S(O)2-C1-C8卤代烷基的脂族基团。
特别优选的脂族基团R2包括C2-C4链烯基、C2-C4炔基、C1-C2卤代烷氧基-C1-C2烷基、C3-C4链烯氧基、C3-C4炔氧基、C1-C4烷基磺酰基、C1-C4烷氧基、C1-C4烷氧羰基和S(O)2-C1-C4烷基。特别优选CH=CH2、CH=CHCH3、CH2OCH2CF3、OC2H5、OCH2CH=CH2、OCH2C≡CH、OCH2CH2OCH3、COOCH3、COOC2H5、SO2CH3、SO2C2H5和SO2CH(CH3)2。
在另一优选方面,R2与R1或R3一起形成含有1、2、3或4个选自O、N和S的杂原子且可以部分或完全被基团Rb取代的5-10员单环或双环饱和或部分不饱和环。与带有基团R1-R5的苯基一起,得到9-15员双环或三环体系,任选为杂环体系。例如合适的是下列:2,3-二氢苯并[b]噻吩-1,1-二氧化物、二氢苯并噻喃-1,1-二氧化物、2,3-二氢苯并[1,4]二噻烯(dithiin)-1,1,4,4-四氧化物、3H-苯并噻唑-2-酮、喹啉和邻磺酰苯甲酰亚胺(saccharin)。
优选R2与R1或R3一起形成5或6员单环饱和或部分不饱和环。
包含与萘啶酮(naphthyridinone)骨架相连的苯基以及R1和R2的优选双环体系例如为基团A-D:
#表示与骨架的键。
包含与萘啶酮骨架相连的苯基以及R2和R3的优选双环和三环体系含有1或2个硫原子和任选1个氮原子。优选基团E-L:
在基团A-L中,基团Rb相互独立地优选为卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C3-C4链烯基、C3-C4炔基、=N-C1-C4烷氧基。
其中R2为基团A-L之一的式I化合物对应于式I.A-I.L。
在式I.A-I.L中,Rb优选为卤素、C1-C4烷基、C1-C4烷氧基或C1-C4卤代烷基。
下列实例代表了特别优选的基团A-L:
R3A、R3B、R3C和R3D优选为卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基,尤其是F、Cl、Br、CH3、CF3或OCH3。
RbE1、RbE2优选为H、C1-C4烷基或C1-C4烷氧基,RbE1尤其为H或CH3;RbE2为H、CH3或OCH3。
RbJ1优选为C1-C4卤代烷氧基,尤其是OCH2CH2F。
RbJ2优选为C1-C4烷氧基,尤其是OCH3或OCH2CH3。
RbL优选为C1-C4烷基或C3-C4链烯基,尤其是CH3、CH2CH3、CH2CH2CH3、CH(CH3)2或CH2CH=CH2。
在式I化合物的另一优选实施方案中,A为N。这些化合物对应于式I.2:
其中各变量具有开头所定义的含义,优选如上所述那些。尤其优选在式I.2的化合物中,基团
R1为硝基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基或C1-C4烷基磺酰基,尤其是NO2、CH3、CF3、CH2OCH2CH2OCH3、OCH3、OCF3、OCHF2、SCF3、SCHF2、SO2CH3;
R3为H、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基,尤其是H、CN、NO2、CH3、CH2CH3、CF3、CHF2、OCH3、OCF3、OCHF2、SCH3、SO2CH3或SO2CH2CH3。
在式I化合物,尤其是式I.1化合物的另一优选实施方案中,R3为氢、卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、S(O)n-C1-C4烷基或S(O)n-C1-C4卤代烷基,其中n优选为0或2。特别优选R3选自H、F、Cl、Br、CN、NO2、CH3、CF3、CHF2、OCH3、OCF3、OCHF2、SCH3、SCF3、SCHF2、SO2CH3、SO2CH2CH3。
在式I化合物的另一优选实施方案中,R4为氢或卤素,特别优选H、F或Cl,尤其是H。
在式I化合物的另一优选实施方案中,R5为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷氧基或C1-C4卤代烷硫基,特别优选H、CH3、CF3、CHF2、OCH3、OCF3、OCHF2、SCH3、SCF3、SCHF2,尤其是H。
在式I化合物的另一优选实施方案中,基团R6和R7中至少一个,优选两个为氢。
在优选实施方案中,X为O。
在另一实施方案中,X为S。
在另一实施方案中,X为NRx。
在优选实施方案中,Y为O。
在另一实施方案中,Y为S。
Rx优选为H,C1-C6烷基,如CH3、C2H5、n-C3H7、CH(CH3)2、n-C3H9或C(CH3)3,C3-C6环烷基-C1-C4烷基,如环丙基甲基,C3-C6链烯基,如CH2CH=CH2、CH2C(CH3)=CH2、CH2CH2H=CH2、CH2CH2C(CH3)-CH2、CH2CH2CH2CH=CH2、CH2CH2CH2C(CH3)=CH2,或任选取代的苯基,如C6H5、4-CH3-C6H4、4-F-C6H4或S(O)n-RN,其中RN为C1-C6卤代烷基如CH2CF3,CH2CHF2。
另一实施方案涉及式I化合物的N-氧化物。
另一实施方案涉及式I化合物的盐,尤其是可以通过季化吡啶氮原子而得到的那些,这优选可以通过将式I化合物烷基化或芳基化而进行。所述化合物的优选盐因此是N-烷基盐,尤其是N-甲基盐,以及N-苯基盐。
尤其考虑到其应用,优选汇编在下表中的式I化合物,这些化合物对应于式I.1A和I.2A。此外,对表中取代基所提到的基团本身为所述取代基的特别优选方面,与其中提到它们的组合无关。
表1
其中X和Y为O,R为OH,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表2
其中X和Y为O,R为OCH2CH=CH2,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表3
其中X和Y为O,R为OCH2C≡CH,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表4
其中X和Y为O,R为OH,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表5
其中X和Y为O,R为OCH2CH=CH2,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表6
其中X和Y为O,R为OCH2C≡CH,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表7
其中X和Y为O,R为OH,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表8
其中X和Y为O,R为OCH2CH=CH2,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表9
其中X和Y为O,R为OCH2C≡CH,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表10
其中X和Y为O,R为OH,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表11
其中X和Y为O,R为OCH2CH=CH2,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表12
其中X和Y为O,R为OCH2C≡CH,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表13
其中X和Y为O,R为OH,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表14
其中X和Y为O,R为OCH2CH=CH2,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表15
其中X和Y为O,R为OCH2C≡CH,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表16
其中X为O,Y为S,R为OH,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表17
其中X为O,Y为S,R为OCH2CH=CH2,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表18
其中X为O,Y为S,R为OCH2C≡CH,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表19
其中X为O,Y为S,R为OH,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表20
其中X为O,Y为S,R为OCH2CH=CH2,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表21
其中X为O,Y为S,R为OCH2C≡CH,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表22
其中X为O,Y为S,R为OH,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表23
其中X为O,Y为S,R为OCH2CH=CH2,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表24
其中X为O,Y为S,R为OCH2C≡CH,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表25
其中X为O,Y为S,R为OH,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表26
其中X为O,Y为S,R为OCH2CH=CH2,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表27
其中X为O,Y为S,R为OCH2C≡CH,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表28
其中X为O,Y为S,R为OH,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表29
其中X为O,Y为S,R为OCH2CH=CH2,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表30
其中X为O,Y为S,R为OCH2C≡CH,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表31
其中X为S,Y为O,R为OH,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表32
其中X为S,Y为O,R为OCH2CH=CH2,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表33
其中X为S,Y为O,R为OCH2C≡CH,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表34
其中X为S,Y为O,R为OH,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表35
其中X为S,Y为O,R为OCH2CH=CH2,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表36
其中X为S,Y为O,R为OCH2C≡CH,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表37
其中X为S,Y为O,R为OH,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表38
其中X为S,Y为O,R为OCH2CH=CH2,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表39
其中X为S,Y为O,R为OCH2C≡CH,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表40
其中X为S,Y为O,R为OH,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表41
其中X为S,Y为O,R为OCH2CH=CH2,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表42
其中X为S,Y为O,R为OCH2C≡CH,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表43
其中X为S,Y为O,R为OH,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表44
其中X为S,Y为O,R为OCH2CH=CH2,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表45
其中X为S,Y为O,R为OCH2C≡CH,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表46
其中X和Y为S,R为OH,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表47
其中X和Y为S,R为OCH2CH=CH2,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表48
其中X和Y为S,R为OCH2C≡CH,R5为H且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表49
其中X和Y为S,R为OH,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表50
其中X和Y为S,R为OCH2CH=CH2,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表51
其中X和Y为S,R为OCH2C≡CH,R5为CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表52
其中X和Y为S,R为OH,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表53
其中X和Y为S,R为OCH2CH=CH2,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表54
其中X和Y为S,R为OCH2C≡CH,R5为CH2CH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表55
其中X和Y为S,R为OH,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表56
其中X和Y为S,R为OCH2CH=CH2,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表57
其中X和Y为S,R为OCH2C≡CH,R5为OCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表58
其中X和Y为S,R为OH,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表59
其中X和Y为S,R为OCH2CH=CH2,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表60
其中X和Y为S,R为OCH2C≡CH,R5为SCH3且R1、R3和合适的话R2的组合对化合物而言在每种情况下对应于表A的一行或者如表A.1或A.2所述的式I化合物
表A
对应于式I.1A和I.2A的式I化合物
#1表征2位的键(基团R1)
#2表征3位的键(基团R2)
#3表征4位的键(基团R3)
表A.1
还尤其优选化合物A.1-1、A.1-8、A.1-15、A.1-22、A.1-29、A.1-36、A.1-43、A.1-50、A.1-57、A.1-64、A.1-71、A.1-78、A.1-85、A.1-92、A.1-99、A.1-106、A.1-113、A.1-120、A.1-127、A.1-134、A.1-141、A.1-148、A.1-155、A.1-162、A.1-169、A.1-176、A.1-183、A.1-199、A.1-206、A.1-213、A.1-220、A.1-227、A.1-234、A.1-241、A.1-248、A.1-255、A.1-262、A.1-269、A.1-276、A.1-283、A.1-290、A.1-297、A.1-304、A.1-311、A.1-318、A.1-325、A.1-332、A.1-339、A.1-346、A.1-353、A.1-360、A.1-367、A.1-374、A.1-381、A.1-397、A.1-404、A.1-411、A.1-418、A.1-425、A.1-432、A.1-439、A.1-446、A.1-453、A.1-460、A.1-467、A.1-474、A.1-481、A.1-488、A.1-495、A.1-502、A.1-509、A.1-516、A.1-523、A.1-530、A.1-537、A.1-544、A.1-551、A.1-558、A.1-565、A.1-572、A.1-579、A.1-595、A.1-602、A.1-609、A.1-616、A.1-623、A.1-630、A.1-637、A.1-644、A.1-651、A.1-658、A.1-665、A.1-672、A.1-679、A.1-679、A.1-686、A.1-693、A.1-700、A.1-707、A.1-714、A.1-721、A.1-728、A.1-735、A.1-742、A.1-749、A.1-756、A.1-763、A.1-770、A.1-777、A.1-793、A.1-800、A.1-807、A.1-814、A.1-821、A.1-828、A.1-835、A.1-842、A.1-849、A.1-856、A.1-863、A.1-870、A.1-877、A.1-884、A.1-891、A.1-898、A.1-905、A.1-912、A.1-919、A.1-926、A.1-933、A.1-940、A.1-947、A.1-954、A.1-961、A.1-968、A.1-975、A.1-991、A.1-998、A.1-1005、A.1-1012、A.1-1019、A.1-1026、A.1-1033、A.1-1040、A.1-1047、A.1-1054、A.1-1061、A.1-1068、A.1-1075、A.1-1082、A.1-1089、A.1-1096、A.1-1103、A.1-1110、A.1-1117、A.1-1124、A.1-1131、A.1-1138、A.1-1145、A.1-1152、A.1-1159、A.1-1166和A.1-1173,它们与相应化合物A-1、A-8、A-15、A-22、A-29、A-36、A-43、A-50、A-57、A-64、A-71、A-78、A-85、A-92、A-99、A-106、A-113、A-120、A-127、A-134、A-141、A-148、A-155、A-162、A-169、A-176、A-183、A-199、A-206、A-213、A-220、A-227、A-234、A-241、A-248、A-255、A-262、A-269、A-276、A-283、A-290、A-297、A-304、A-311、A-318、A-325、A-332、A-339、A-346、A-353、A-360、A-367、A-374、A-381、A-397、A-404、A-411、A-418、A-425、A-432、A-439、A-446、A-453、A-460、A-467、A-474、A-481、A-488、A-495、A-502、A-509、A-516、A-523、A-530、A-537、A-544、A-551、A-558、A-565、A-572、A-579、A-595、A-602、A-609、A-616、A-623、A-630、A-637、A-644、A-651、A-658、A-665、A-672、A-679、A-679、A-686、A-693、A-700、A-707、A-714、A-721、A-728、A-735、A-742、A-749、A-756、A-763、A-770、A-777、A-793、A-800、A-807、A-814、A-821、A-828、A-835、A-842、A-849、A-856、A-863、A-870、A-877、A-884、A-891、A-898、A-905、A-912、A-919、A-926、A-933、A-940、A-947、A-954、A-961、A-968、A-975、A-991、A-998、A-1005、A-1012、A-1019、A-1026、A-1033、A-1040、A-1047、A-1054、A-1061、A-1068、A-1075、A-1082、A-1089、A-1096、A-1103、A-1110、A-1117、A-1124、A-1131、A-1138、A-1145、A-1152、A-1159、A-1166和A-1173的不同仅在于R3为F。
表A.2
还尤其优选化合物A.2-1、A.2-8、A.2-15、A.2-22、A.2-29、A.2-36、A.2-43、A.2-50、A.2-57、A.2-64、A.2-71、A.2-78、A.2-85、A.2-92、A.2-99、A.2-106、A.2-113、A.2-120、A.2-127、A.2-134、A.2-141、A.2-148、A.2-155、A.2-162、A.2-169、A.2-176、A.2-183、A.2-199、A.2-206、A.2-213、A.2-220、A.2-227、A.2-234、A.2-241、A.2-248、A.2-255、A.2-262、A.2-269、A.2-276、A.2-283、A.2-290、A.2-297、A.2-304、A.2-311、A.2-318、A.2-325、A.2-332、A.2-339、A.2-346、A.2-353、A.2-360、A.2-367、A.2-374、A.2-381、A.2-397、A.2-404、A.2-411、A.2-418、A.2-425、A.2-432、A.2-439、A.2-446、A.2-453、A.2-460、A.2-467、A.2-474、A.2-481、A.2-488、A.2-495、A.2-502、A.2-509、A.2-516、A.2-523、A.2-530、A.2-537、A.2-544、A.2-551、A.2-558、A.2-565、A.2-572、A.2-579、A.2-595、A.2-602、A.2-609、A.2-616、A.2-623、A.2-630、A.2-637、A.2-644、A.2-651、A.2-658、A.2-665、A.2-672、A.2-679、A.2-679、A.2-686、A.2-693、A.2-700、A.2-707、A.2-714、A.2-721、A.2-728、A.2-735、A.2-742、A.2-749、A.2-756、A.2-763、A.2-770、A.2-777、A.2-793、A.2-800、A.2-807、A.2-814、A.2-821、A.2-828、A.2-835、A.2-842、A.2-849、A.2-856、A.2-863、A.2-870、A.2-877、A.2-884、A.2-891、A.2-898、A.2-905、A.2-912、A.2-919、A.2-926、A.2-933、A.2-940、A.2-947、A.2-954、A.2-961、A.2-968、A.2-975、A.2-991、A.2-998、A.2-1005、A.2-1012、A.2-1019、A.2-1026、A.2-1033、A.2-1040、A.2-1047、A.2-1054、A.2-1061、A.2-1068、A.2-1075、A.2-1082、A.2-1089、A.2-1096、A.2-1103、A.2-1110、A.2-1117、A.2-1124、A.2-1131、A.2-1138、A.2-1145、A.2-1152、A.2-1159、A.2-1166和A.2-1173,它们与相应化合物A-1、A-8、A-15、A-22、A-29、A-36、A-43、A-50、A-57、A-64、A-71、A-78、A-85、A-92、A-99、A-106、A-113、A-120、A-127、A-134、A-141、A-148、A-155、A-162、A-169、A-176、A-183、A-199、A-206、A-213、A-220、A-227、A-234、A-241、A-248、A-255、A-262、A-269、A-276、A-283、A-290、A-297、A-304、A-311、A-318、A-325、A-332、A-339、A-346、A-353、A-360、A-367、A-374、A-381、A-397、A-404、A-411、A-418、A-425、A-432、A-439、A-446、A-453、A-460、A-467、A-474、A-481、A-488、A-495、A-502、A-509、A-516、A-523、A-530、A-537、A-544、A-551、A-558、A-565、A-572、A-579、A-595、A-602、A-609、A-616、A-623、A-630、A-637、A-644、A-651、A-658、A-665、A-672、A-679、A-679、A-686、A-693、A-700、A-707、A-714、A-721、A-728、A-735、A-742、A-749、A-756、A-763、A-770、A-777、A-793、A-800、A-807、A-814、A-821、A-828、A-835、A-842、A-849、A-856、A-863、A-870、A-877、A-884、A-891、A-898、A-905、A-912、A-919、A-926、A-933、A-940、A-947、A-954、A-961、A-968、A-975、A-991、A-998、A-1005、A-1012、A-1019、A-1026、A-1033、A-1040、A-1047、A-1054、A-1061、A-1068、A-1075、A-1082、A-1089、A-1096、A-1103、A-1110、A-1117、A-1124、A-1131、A-1138、A-1145、A-1152、A-1159、A-1166和A-1173的不同仅在于R3为Cl。
化合物I及其可农用盐适合以异构体混合物形式和纯异构体形式用作除草剂。它们适合直接使用或适合以适当配制的组合物使用。包含化合物I(尤其是其优选方面)的除草组合物非常有效地防治非作物区域的植物生长,尤其是在高施用率下。它们在诸如小麦、稻、玉米、大豆和棉花的作物中作用于阔叶杂草和禾本科杂草而不对农作物引起任何显著的损害。该效果主要在低施用率下观察到。
取决于所述施用方法,化合物I,尤其是其优选方面,或者包含它们的组合物可以额外用于许多其他农作物以消除不希望的植物。合适的作物实例如下:洋葱(Allium cepa)、凤梨(Ananas comosus)、落花生(Arachishypogaea)、石刁柏(Asparagus officinalis)、燕麦(Avena sativa)、甜菜(Beta vulgaris spec.altissima)、甜菜(Beta vulgaris spec.rapa)、欧洲油菜(Brassica napus var.napus)、芜青甘蓝(Brassica napus var.napobrassica)、芜青(Brassica rapa var.silvestris)、羽衣甘蓝(Brassicaoleracea)、黑芥(Brassica nigra)、大叶茶(Camellia sinensis)、红花(Carthamus tinctorius)、美国山核桃(Carya illinoinensis)、柠檬(Citruslimon)、甜橙(Citrus sinensis)、小果咖啡(Coffea arabica)(中果咖啡(Coffea canephora)、大果咖啡(Coffea liberica))、黄瓜(Cucumissativus)、狗牙根(Cynodon dactylon)、胡萝卜(Daucus carota)、油棕(Elaeis guineensis)、欧洲草莓(Fragaria vesca)、大豆(Glycine max)、陆地棉(Gossypium hirsutum)(树棉(Gossypium arboreum)、草棉(Gossypiumherbaceum)、Gossypium vitifolium)、向日葵(Helianthus annuus)、Heveabrasiliensis、大麦(Hordeum vulgare)、啤酒花(Humulus lupulus)、甘薯(Ipomoea batatas)、核桃(Juglans regia)、兵豆(Lens culinaris)、亚麻(Linum usitatissimum)、番茄(Lycopersicon lycopersicum)、苹果属(Malusspec.)、木薯(Manihot esculenta)、紫苜蓿(Medicago sativa)、芭蕉属(Musa spec.)、烟草(Nicotiana tabacum)(黄花烟草(N.rustica))、油橄榄(Olea europaea)、稻(Oryza sativa)、金甲豆(Phaseolus lunatus)、菜豆(Phaseolus vulgaris)、欧洲云杉(Picea abies)、松属(Pinus spec.)、开心果(Pistacia vera)、Pisum sativum、欧洲甜樱桃(Prunus avium)、Prunuspersica、西洋梨(Pyrus communis)、杏(Prunus armeniaca)、欧洲酸樱桃(Prunus cerasus)、扁桃(Prunus dulcis)和欧洲李(Prunus domestica)、Ribes sylvestre、蓖麻(Ricinus communis)、甘蔗(Saccharumofficinarum)、黑麦(Secale cereale)、白芥(Sinapis alba)、马铃薯(Solanumtuberosum)、两色蜀黍(Sorghum bicolor)(高粱(S.vulgare))、可可树(Theobroma cacao)、红车轴草(Trifolium pratense)、普通小麦(Triticumaestivum)、小黑麦(Triticale)、硬粒小麦(Triticum durum)、蚕豆(Viciafaba)、葡萄(Vitis vinifera)、玉蜀黍(Zea mays)。
术语“农作物”还包括已经通过育种、诱变或基因工程修饰的植物。基因修饰植物是其基因材料以在自然条件下不通过杂交、突变或自然重组(即基因信息的重组)发生的方式修饰的植物。此处通常将一个或多个基因整合到植物的基因材料中以改善植物性能。
因此,术语“农作物”还包括已经通过育种和基因工程而获得对某些类别的除草剂的耐受性的植物,所述除草剂例如羟基苯基丙酮酸双加氧酶(HPPD)抑制剂,乙酰乳酸合成酶(ALS)抑制剂如磺酰脲类(EP-A-0257993,US 5,013,659)或咪唑啉酮类(例如参见US 6,222,100、WO01/82685、WO 00/026390、WO 97/41218、WO 98/002526、WO98/02527、WO 04/106529、WO 05/20673、WO 03/014357、WO03/13225、WO 03/14356、WO 04/16073),烯醇丙酮酰莽草酸3-磷酸合成酶(EPSPS)抑制剂如草甘膦(glyphosate)(例如参见WO 92/00377),谷氨酰胺合成酶(GS)抑制剂如草铵膦(glufosinate)(例如参见EP-A-0242236、EP-A-242246)或苯腈类(oxynil)除草剂(例如参见US 5,559,024)。
许多农作物如油菜已经借助常规育种(诱变)方法而耐受咪唑啉酮类如咪草啶酸(imazamox)。已经借助基因工程方法产生耐受草甘膦或草铵膦的农作物如大豆、棉花、玉米、甜菜和油菜,它们可以以商标名(耐受草甘膦)和Liberty(耐受草铵膦)市购。
因此,术语“农作物”还包括借助基因工程而产生一种或多种毒素如芽孢杆菌属(Bacillus)细菌菌株的那些的植物。由该类基因修饰植物产生的毒素例如包括芽孢杆菌属,尤其是苏云金芽孢杆菌(B.thuringiensis)的杀虫蛋白如内毒素Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1、Cry9c、Cry34Ab1或Cry35Ab1;或无性杀虫蛋白(VIP),例如VIP1、VIP2、VIP3或VIP3A;线虫定居细菌的杀虫蛋白,例如发光杆菌属(Photorhabdus)或致病杆菌属(Xenorhabdus);动物有机体的毒素如黄蜂、蜘蛛或蝎子毒素;真菌毒素,例如来自链霉菌属(Streptomycetes);植物凝集素,例如来自豌豆或大麦;凝集素,蛋白酶抑制剂,例如胰蛋白酶抑制剂,丝氨酸蛋白酶抑制剂,patatin,半胱氨酸蛋白酶抑制剂或木瓜蛋白酶抑制剂,核糖体失活蛋白(RIP),例如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽蛋白、皂草素或异株腹泻毒蛋白(bryodin);类固醇代谢酶,例如3-羟基类固醇氧化酶、蜕皮甾类-IDP糖基转移酶、胆固醇氧化酶、蜕皮激素抑制剂或HMG-CoA还原酶;离子通道阻断剂,例如钠通道或钙通道抑制剂;保幼激素酯酶;利尿激素受体(helicokinin受体);芪合成酶,联苄合成酶,壳多糖酶和葡聚糖酶。在植物中,这些毒素还可以作为前毒素、杂合蛋白或截短的或其他方面改性的蛋白产生。杂合蛋白的特征在于不同蛋白域的新型组合(例如参见WO2002/015701)。该类毒素或产生这些毒素的基因修饰植物的其他实例公开于EP-A 374753、WO 93/07278、WO 95/34656、EP-A 427529、EP-A451878、WO 03/18810和WO 03/52073中。生产这些基因修饰植物的方法对本领域熟练技术人员是已知的且例如公开于上述出版物中。许多上述毒素赋予产生它们的植物以对所有分类学上为节肢动物的害虫,尤其是甲虫(鞘翅目(Coeleropta))、双翅目昆虫(双翅目(Diptera))和蝴蝶(鳞翅目(Lepidoptera))以及线虫(线虫纲(Nematoda))的耐受性。
对杀虫毒素产生一个或多个基因编码的基因修饰植物例如描述于上述出版物中,它们中的一些可市购,例如(产生毒素Cry1Ab的玉米品种),Plus(产生毒素Cry1Ab和Cry3Bb1的玉米品种),(产生毒素Cry9c的玉米品种),RW(产生毒素Cry34Ab1、Cry35Ab1和酶膦丝菌素-N-乙酰转移酶[PAT]的玉米品种);33B(产生毒素Cry1Ac的棉花品种),I(产生毒素Cry1Ac的棉花品种),II(产生毒素Cry1Ac和Cry2Ab2的棉花品种);(产生VIP毒素的棉花品种);(产生毒素Cry3A的土豆品种); Bt11(例如CB)和法国Syngenta Seeds SAS的Bt176(产生毒素Cry1Ab和PAT酶的玉米品种),法国Syngenta Seeds SAS的MIR604(产生毒素Cry3A的修饰译本的玉米品种,见WO 03/018810),比利时Monsanto Europe S.A.的MON 863(产生毒素Cry3Bb1的玉米品种),比利时Monsanto Europe S.A.的IPC 531(产生毒素Cry1Ac的修饰译本的棉花品种)和比利时Pioneer Overseas Corporation的1507(产生毒素Cry1F和PAT酶的玉米品种)。
因此,术语“农作物”还包括借助基因工程产生一种或多种更强壮或对细菌、病毒或真菌病原体的耐受性增强的蛋白质的植物,例如与发病机理相关的蛋白(PR蛋白,参见EP-A 0392225),抗性蛋白(例如产生两种针对来自野生墨西哥土豆Solanum bulbocastanum的致病疫霉(Phytophthorainfestans)的抗性基因的土豆品种)或T4溶菌酶(例如通过产生该蛋白而耐受细菌如Erwinia amylvora的土豆栽培品种)。
因此,术语“农作物”还包括已经借助基因工程方法,例如通过提高潜在产量(例如生物质、谷粒产量、淀粉、油或蛋白质含量),对干旱、盐或其他极限环境因素或对害虫以及真菌、细菌和病毒病原体的耐受性而改善生产量的植物。
此外,已经发现式I化合物还适于植物部分的脱叶和/或干燥,对此合适的是农作物如棉花、土豆、油菜、向日葵、大豆或蚕豆,尤其是棉花。就此而言,已经发现用于植物干燥和/或脱叶的组合物、制备这些组合物的方法以及使用式I化合物使植物干燥和/或脱叶的方法。
作为干燥剂,式I化合物特别适于干燥农作物如土豆、油菜、向日葵和大豆以及禾谷类的地面上部分。这使得这些重要农作物的完全机械化收获成为可能。
还具有经济益处的是促进柑橘类水果、橄榄和其他品种的仁果、核果和坚果的收获,这通过在一定时间期限内集中裂开或降低对树的粘附而成为可能。相同的机理,即促进水果部分或叶部分与植物的枝部分之间产生脱离组织对于有用植物,尤其是棉花的易控脱叶也是必要的。
此外,各棉花植株成熟的时间间隔缩短导致收获后的纤维质量提高。
化合物I或包含化合物I的除草组合物例如可以以即喷水溶液,粉末,悬浮液以及高度浓缩的水性、油性或其它悬浮液或分散体,乳液,油分散体,糊,粉剂,撒播用材料或颗粒的形式通过喷雾、雾化、撒粉、撒播、浇灌或处理种子或与种子混合而使用。使用形式取决于意欲的目的;在每种情况下都应确保本发明活性成分的最佳可能分布。
除草组合物包含除草有效量的至少一种式I化合物或I的可农用盐和常用于配制作物保护剂的助剂。
常用于配制作物保护剂的助剂实例是惰性助剂,固体载体,表面活性剂(如分散剂、保护性胶体、乳化剂、润湿剂和增粘剂),有机和无机增稠剂,杀菌剂,防冻剂,消泡剂,合适的话还有着色剂以及用于种子配制剂的粘合剂。
增稠剂(即赋予配制剂以改性的流动性能,即静止状态下的高粘度和运动状态下的低粘度的化合物)的实例是多糖,如黄原胶(来自Kelco的),23(Rhone Poulenc)或(来自R.T.Vanderbilt),以及有机和无机片状矿物,如(来自Engelhardt)。
可以加入杀菌剂以稳定含水除草配制剂。杀菌剂实例是基于双氯芬和苄醇半缩甲醛的杀菌剂(ICI的或Thor Chemie的RS以及Rohm&Haas的MK),还有异噻唑啉酮衍生物,如烷基异噻唑啉酮类和苯并异噻唑啉酮类(Thor Chemie的Acticide MBS)。
防冻剂实例是乙二醇、丙二醇、脲或甘油。
着色剂的实例是微水溶性颜料和水溶性染料。可以提到的实例是以如下名称已知的染料:若丹明B,C.I.颜料红112和C.I.溶剂红1,以及颜料蓝15:4,颜料蓝15:3,颜料蓝15:2,颜料蓝15:1,颜料蓝80,颜料黄1,颜料黄13,颜料红112,颜料红48:2,颜料红48:1,颜料红57:1,颜料红53:1,颜料橙43,颜料橙34,颜料橙5,颜料绿36,颜料绿7,颜料白6,颜料棕25,碱性紫10,碱性紫49,酸性红51,酸性红52,酸性红14,酸性蓝9,酸性黄23,碱性红10,碱性红108。
粘合剂的实例是聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和纤基乙酸钠。
合适的惰性助剂例如为下列物质:中沸点到高沸点的矿物油馏分如煤油和柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如石蜡,四氢化萘,烷基化萘及其衍生物,烷基化苯及其衍生物,醇类如甲醇、乙醇、丙醇、丁醇和环己醇,酮类如环己酮或强极性溶剂,例如胺类如N-甲基吡咯烷酮,以及水。
固体载体为矿土如硅石、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁和氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵和脲类以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉或其它固体载体。
合适的表面活性剂(助剂、润湿剂、增粘剂、分散剂以及乳化剂)是芳族磺酸如木素磺酸(例如Borrespers类型,Borregaard)、苯酚磺酸、萘磺酸(Morwet类型,Akzo Nobel)和二丁基萘磺酸(Nekal类型,BASF SE)以及脂肪酸的碱金属盐、碱土金属盐和铵盐,烷基-和烷基芳基磺酸盐,烷基硫酸盐,月桂基醚硫酸盐和脂肪醇硫酸盐,以及硫酸化十六-、十七-和十八烷醇的盐,还有脂肪醇乙二醇醚的盐,磺化萘及其衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化异辛基-、辛基-或壬基酚,烷基苯基或三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯烷基醚,月桂醇聚乙二醇醚乙酸酯,山梨糖醇酯,木素亚硫酸盐废液和蛋白质,变性蛋白质,多糖(如甲基纤维素),疏水改性的淀粉,聚乙烯醇(Mowiol类型,Clariant),聚羧酸盐类(BASF SE,Sokalan类型),聚烷氧基化物,聚乙烯胺(BASF SE,Lupamine类型),聚乙烯亚胺(BASF SE,Lupasol类型),聚乙烯基吡咯烷酮及其共聚物。
粉末、撒播材料和粉剂可以通过将活性成分与固体载体混合或研磨来制备。
颗粒如包衣颗粒、浸渍颗粒和均质颗粒可以通过使活性成分与固体载体粘附而制备。
含水使用形式可以通过添加水由乳液浓缩物、悬浮液、糊、可湿性粉末或水分散性颗粒制备。为了制备乳液、糊或油分散体,可以借助湿润剂、增粘剂、分散剂或乳化剂将式I或Ia化合物直接或溶于油或溶剂之后在水中均化。或者还可以制备包含活性物质、湿润剂、增粘剂、分散剂或乳化剂以及需要的话,溶剂或油的浓缩物,该类浓缩物适于用水稀释。
式I化合物在即用制剂中的浓度可以在宽范围内变化。配制剂通常包含0.001-98重量%,优选0.01-95重量%至少一种活性化合物。活性化合物以90-100%,优选95-100%(根据NMR光谱)的纯度使用。
配制剂或即用制剂还可以包含酸、碱或缓冲剂体系,合适的实例是磷酸或硫酸,或尿素或氨。
本发明化合物I例如可以按如下配制:
1.用水稀释的产品
A水溶性浓缩物
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。这得到活性化合物含量为10重量%的配制剂。
B分散性浓缩物
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。活性化合物含量为20重量%。
C可乳化浓缩物
将15重量份活性化合物溶于75重量份有机溶剂(如烷基芳烃)中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液。该配制剂的活性化合物含量为15重量%。
D乳液
将25重量份活性化合物溶于35重量份有机溶剂(如烷基芳烃)中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(Ultraturrax)将该混合物引入30重量份水中并制成均质乳液。用水稀释得到乳液。该配制剂的活性化合物含量为25重量%。
E悬浮液
在搅拌式球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。该配制剂中活性化合物含量为20重量%。
F水分散性颗粒和水溶性颗粒
将50重量份活性化合物细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为50重量%。
G水分散性粉末和水溶性粉末
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为75重量%。
H凝胶配制剂
在球磨机中研磨20重量份活性化合物、10重量份分散剂、1重量份胶凝剂和70重量份水或有机溶剂,得到细悬浮液。用水稀释得到活性化合物含量为20重量%的稳定悬浮液。
2.不经稀释而施用的产品
I粉剂
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到活性化合物含量为5重量%的撒粉粉末。
J颗粒(GR,FG,GG,MG)
将0.5重量份活性化合物细碎研磨并结合99.5重量份载体。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的活性化合物含量为0.5重量%的颗粒。
K ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到不经稀释而施用的活性化合物含量为10重量%的产品。
化合物I或包含它们的除草组合物可以出苗前或出苗后施用,或者与农作物的种子一起施用。还可以通过施用被除草组合物或活性化合物预处理的农作物的种子而施用除草组合物或活性化合物。若活性化合物不能被某些农作物良好地耐受,则可以使用其中借助喷雾设备喷雾除草组合物以使它们尽可能不接触敏感农作物的叶子,而活性成分到达生长在下面的不希望的植物的叶子或裸露的土壤表面的施用技术(后引导,最后耕作程序)。
在另一实施方案中,可以通过处理种子而施用式I化合物或其除草组合物。
种子的处理基本包括所有本领域熟练技术人员熟知的基于本发明式I化合物或由其制备的组合物的程序(拌种、种子包衣、种子撒粉、种子浸泡、种子包膜、种子多层包衣、种子包壳、种子浸滴和种子造粒)。这里可以加以稀释或不加稀释地施用除草组合物。
术语种子包括所有类型的种子,如玉米、种子、果实、块茎、插条和类似形式。这里优选术语种子描述的是玉米和种子。
所用种子可以是上述有用植物的种子,但还可以是转基因植物或通过常规育种方法得到的植物的种子。
活性化合物的施用率为0.001-3.0kg/ha,优选0.01-1.0kg/ha活性物质(a.s.),取决于防治目标、季节、目标植物和生长阶段。为了处理种子,化合物I通常以0.001-10kg/100kg种子的量使用。
还可能有利的是将式I化合物与安全剂组合使用。安全剂是防止或降低对有用植物的损害而不显著影响式I化合物对不希望的植物的除草作用的化合物。它们可以在播种之前(例如在种子处理中或在插条或秧苗上)和有用植物出苗之前或之后使用。安全剂和式I化合物可以同时或依次使用。合适的安全剂例如为(喹啉-8-氧基)乙酸、1-苯基-5-卤代烷基-1H-1,2,4-***-3-羧酸、1-苯基-4,5-二氢-5-烷基-1H-吡唑-3,5-二羧酸、4,5-二氢-5,5-二芳基-3-异唑羧酸、二氯乙酰胺类、α-肟基苯基乙腈类、苯乙酮肟类、4,6-二卤代-2-苯基嘧啶、N-[[4-(氨基羰基)苯基]磺酰基]-2-苯甲酰胺、1,8-萘二甲酸酐、2-卤代-4-卤代烷基-5-噻唑羧酸、硫代磷酸酯类和O-苯基N-烷基氨基甲酸酯及其可农用盐,以及它们的可农用衍生物如酰胺、酯和硫酯,条件是它们具有酸官能团。
为了拓宽活性谱并获得协同增效效果,可以将式I化合物与大量其他除草或生长调节活性化合物的代表或安全剂混合并联合施用。合适的混合配对例如为1,2,4-噻二唑类,1,3,4-噻二唑类,酰胺类,氨基磷酸及其衍生物,氨基***类,酰替苯胺类,芳氧基/杂芳氧基链烷酸及其衍生物,苯甲酸及其衍生物,苯并噻二嗪酮类,2-芳酰基/杂芳酰基-1,3-环己烷二酮类,杂芳基芳基酮类,苄基异唑烷酮类,间-CF3-苯基衍生物,氨基甲酸酯类,喹啉羧酸及其衍生物,氯代乙酰苯胺类,环己酮肟醚衍生物,二嗪类,二氯丙酸及其衍生物,二氢苯并呋喃类,二氢呋喃-3-酮类,二硝基苯胺类,二硝基苯酚类,二苯基醚类,联吡啶类,卤代羧酸及其衍生物,脲类,3-苯基尿嘧啶类,咪唑类,咪唑啉酮类,N-苯基-3,4,5,6-四氢邻苯二甲酰亚胺类,二唑类,环氧乙烷类,酚类,芳氧基-和杂芳氧基苯氧基丙酸酯,苯基乙酸及其衍生物,2-苯基丙酸及其衍生物,吡唑类,苯基吡唑类,哒嗪类,吡啶羧酸及其衍生物,嘧啶基醚类,磺酰胺类,磺酰脲类,三嗪类,三嗪酮类,***啉酮类,***羧酰胺,尿嘧啶类,苯基吡唑啉类,异唑啉类及其衍生物。
此外,可能有用的是单独或与其他除草剂组合施用化合物I,或者还可以与其他作物保护试剂混合而联合施用化合物I,例如与用于防治害虫或植物病原性真菌或细菌的组合物联合施用化合物I。还令人感兴趣的是与无机盐溶液的溶混性,所述盐溶液用于缓解营养和痕量元素缺乏。还可以加入其他添加剂如非植物毒性油和油浓缩物。
可以与本发明的式I的吡啶化合物组合使用的除草剂实例为:
b1)选自如下的类脂生物合成抑制剂:枯杀达(alloxydim)、枯杀达(alloxydim-sodium)、丁氧环酮(butroxydim)、烯草酮(clethodim)、炔草酯(clodinafop)、炔草酯(clodinafop-propargyl)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop)、氰氟草酯(cyhalofop-butyl)、氯甲草(diclofop)、禾草灵(diclofop-methyl)、唑禾草灵(fenoxaprop)、唑禾草灵(fenoxaprop-ethyl)、高唑禾草灵(fenoxaprop-P)、高唑禾草灵(fenoxaprop-P-ethyl)、吡氟禾草灵(fluazifop)、吡氟禾草灵(fluazifop-butyl)、精吡氟禾草灵(fluazifop-P)、精吡氟禾草灵(fluazifop-P-butyl)、吡氟氯禾灵(haloxyfop)、吡氟氯禾灵(haloxyfop-methyl)、精吡氟氯禾灵(haloxyfop-P)、精吡氟氯禾灵(haloxyfop-P-methyl)、唑酰草胺(metamifop)、唑啉草酯(pinoxaden)、环苯草酮(profoxydim)、喔草酯(propaquizafop)、喹禾灵(quizalofop)、喹禾灵(quizalofop-ethyl)、喹禾灵(四氢糠基酯)(quizalofop-tefuryl)、精喹禾灵(quizalofop-P)、精喹禾灵(quizalofop-P-ethyl)、精喹禾灵(四氢糠基酯)(quizalofop-P-tefuryl)、稀禾定(sethoxydim)、醌肟草(tepraloxydim)、肟草酮(tralkoxydim)、呋草黄(benfuresate)、苏达灭(butylate)、草灭特(cycloate)、茅草枯(dalapon)、哌草丹(dimepiperate)、扑草灭(EPTC)、禾草畏(esprocarb)、乙呋草黄(ethofumesate)、四氟丙酸(flupropanate)、草达灭(molinate)、坪草丹(orbencarb)、克草猛(pebulate)、苄草丹(prosulfocarb)、TCA、杀草丹(thiobencarb)、丁草威(tiocarbazil)、野麦畏(triallate)和灭草猛(vernolate);
b2)选自如下的ALS抑制剂:磺氨黄隆(amidosulfuron)、四唑黄隆(azimsulfuron)、苄嘧黄隆(bensulfuron)、苄嘧黄隆(bensulfuron-methyl)、双嘧苯甲酸(bispyribac)、双嘧苯甲酸钠(bispyribac-sodium)、氯嘧黄隆(chlorimuron)、氯嘧黄隆(chlorimuron-ethyl)、绿黄隆(chlorsulfuron)、醚黄隆(cinosulfuron)、唑嘧磺胺酸(cloransulam)、唑嘧磺胺盐(cloransulam-methyl)、环丙黄隆(cyclosulfamuron)、唑嘧磺胺(diclosulam)、胺苯黄隆(ethametsulfuron)、胺苯黄隆(ethametsulfuron-methyl)、乙氧嘧黄隆(ethoxysulfuron)、啶嘧黄隆(flazasulfuron)、双氟磺草胺(florasulam)、氟酮磺隆(flucarbazone)、氟酮磺隆钠(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氟唑啶草(flumetsulam)、氟定黄隆(flupyrsulfuron)、氟定黄隆(flupyrsulfuron-methyl-sodium)、甲酰氨磺隆(foramsulfuron)、吡氯黄隆(halosulfuron)、吡氯黄隆(halosulfuron-methyl)、咪草酯(imazamethabenz)、咪草酯(imazamethabenz-methyl)、咪草啶酸(imazamox)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr)、啶咪黄隆(imazosulfuron)、碘黄隆(iodosulfuron)、碘甲黄隆钠(iodosulfuron-methyl-sodium)、甲基二磺隆(mesosulfuron)、唑草磺胺(metosulam)、甲黄隆(metsulfuron)、甲黄隆(metsulfuron-methyl)、烟嘧黄隆(nicosulfuron)、嘧苯胺磺隆(orthosulfamuron)、环丙氧黄隆(oxasulfuron)、五氟磺草胺(penoxsulam)、氟嘧黄隆(primisulfuron)、氟嘧黄隆(primisulfuron-methyl)、丙苯磺隆(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、氟丙黄隆(prosulfuron)、吡嘧黄隆(pyrazosulfuron)、吡嘧黄隆(pyrazosulfuron-ethyl)、嘧苯草肟(pyribenzoxim)、pyrimisulfan、环酯草醚(pyriftalid)、肟啶草(pyriminobac)、肟啶草(pyriminobac-methyl)、嘧硫苯甲酸(pyrithiobac)、嘧硫苯甲酸钠(pyrithiobac-sodium)、啶磺草胺(pyroxsulam)、玉嘧黄隆(rimsulfuron)、嘧黄隆(sulfometuron)、嘧黄隆(sulfometuron-methyl)、乙黄黄隆(sulfosulfuron)、thiencarbazone、thiencarbazone-methyl、噻黄隆(thifensulfuron)、噻黄隆(thifensulfuron-methyl)、醚苯黄隆(triasulfuron)、苯黄隆(tribenuron)、苯黄隆(tribenuron-methyl)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)和三氟甲磺隆(tritosulfuron);
b3)选自如下的光合成抑制剂:莠灭净(ametryn)、胺唑草酮(amicarbazone)、莠去津(atrazine)、噻草平(bentazone)、噻草平(bentazone-sodium)、除草定(bromacil)、杀草全(bromofenoxim)、溴苯腈(bromoxynil)及其盐和酯、氯溴隆(chlorobromuron)、杀草敏(chloridazone)、绿麦隆(chlorotoluron)、枯草隆(chloroxuron)、草净津(cyanazine)、异苯敌草(desmedipham)、敌草净(desmetryn)、丁隆(dimefuron)、戊草津(dimethametryn)、敌草快阳离子(diquat)、敌草快(diq uat-dibromide)、敌草隆(diuron)、伏草隆(fluometuron)、六嗪同(hexazinone)、碘苯腈(ioxynil)及其盐和酯、异丙隆(isoproturon)、异恶隆(isouron)、卡草灵(karbutilate)、环草定(lenacil)、利谷隆(linuron)、苯嗪草(metamitron)、噻唑隆(methabenzthiazuron)、色满隆(metobenzuron)、甲氧隆(metoxuron)、赛克津(metribuzin)、绿谷隆(monolinuron)、草不隆(neburon)、对草快阳离子(paraquat)、对草快(paraquat-dichloride)、对草快(paraquat-dimetilsulfate)、蔬草灭(pentanochlor)、苯敌草(phenmedipham)、乙苯敌草(phenmedipham-ethyl)、扑灭通(prometon)、扑草净(prometryn)、敌稗(propanil)、扑灭津(propazine)、pyridafol、达草止(pyridate)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、丁唑隆(tebuthiuron)、特草定(terbacil)、甲氧去草净(terbumeton)、特丁津(terbuthylazine)、去草净(terbutryn)、赛二唑素(thidiazuron)和草达津(trietazine);
b4)选自如下的原卟啉原-IX氧化酶抑制剂:氟锁草醚(acifluorfen)、氟锁草醚(acifluorfen-sodium)、唑啶炔草(azafenidin)、bencarbazone、双苯嘧草酮(benzfendizone)、治草醚(bifenox)、氟丙嘧草酯(butafenacil)、氟酮唑草(carfentrazone)、氟酮唑草(carfentrazone-ethyl)、氯硝醚(chlomethoxyfen)、吲哚酮草酯(cinidon-ethyl)、异丙吡草酯(fluazolate)、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、酰亚胺苯氧乙酸(flumiclorac)、酰亚胺苯氧乙酸戊酯(flumiclorac-p entyl)、氟嗪酮(flumioxazin)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚(fluoroglycofen-ethyl)、达草氟(fluthiacet)、达草氟(fluthiacet-methyl)、氟黄胺草醚(fomesafen)、氟硝磺酰胺(halosafen)、乳氟禾草灵(lactofen)、炔丙唑草(oxadiargyl)、恶草灵(oxadiazon)、乙氧氟草醚(oxyfluorfen)、戊唑草(pentoxazone)、氟唑草胺(profluazol)、双唑草腈(pyraclonil)、氟唑草酯(pyraflufen)、氟唑草酯(pyraflufen-ethyl)、嘧啶肟草醚(saflufenacil)、磺胺草唑(sulfentrazone)、噻二唑胺(thidiazimin)、2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶基]-4-氟-N-[(异丙基)甲基氨磺酰基]苯甲酰胺(H-1;CAS 372137-35-4)、[3-[2-氯-4-氟-5-(1-甲基-6-三氟甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-3-基)苯氧基]-2-吡啶氧基]乙酸乙酯(H-2;CAS 353292-31-6)、N-乙基-3-(2,6-二氯-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(H-3;CAS 452098-92-9)、N-四氢糠基-3-(2,6-二氯-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(H-4;CAS915396-43-9)、N-乙基-3-(2-氯-6-氟-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(H-5;CAS 452099-05-7)、N-四氢糠基-3-(2-氯-6-氟-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(H-6;CAS 452100-03-7)、3-[7-氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[1,4]嗪-6-基]-1,5-二甲基-6-硫代-[1,3,5]三嗪烷(triazinan)-2,4-二酮、1,5-二甲基-6-硫代-3-(2,2,7-三氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[b][1,4]嗪-6-基)-1,3,5-三嗪烷-2,4-二酮、2-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)-4,5,6,7-四氢异吲哚-1,3-二酮和1-甲基-6-三氟甲基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)-1H-嘧啶-2,4-二酮;
b5)选自如下的漂白剂除草剂:苯草醚(aclonifen)、杀草强(amitrol)、氟丁酰草胺(beflubutamid)、苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、异恶草酮(clomazone)、吡氟草胺(diflufenican)、氟草同(fluridone)、氟咯草酮(flurochloridone)、呋草酮(flurtamone)、异氟草(isoxaflutole)、甲基磺草酮(mesotrione)、达草灭(norflurazon)、氟吡酰草胺(picolinafen)、pyrasulfutole、吡唑特(pyrazolynate)、苄草唑(pyrazoxyfen)、磺草酮(sulcotrione)、tefuryltrione、tembotrione、topramezone、4-羟基-3-[[2-[(2-甲氧基乙氧基)甲基]-6-三氟甲基-3-吡啶基]羰基]双环[3.2.1]辛-3-烯-2-酮(H-7;CAS 352010-68-5)和4-(3-三氟甲基苯氧基)-2-(4-三氟甲基苯氧基)嘧啶(H-8;CAS 180608-33-7);
b6)选自如下的EPSP合成酶抑制剂:草甘膦、草甘膦异丙胺盐(glyphosate-isopropylammonium)和草硫膦(glyphosate-trimesium)(sulfosate);
b7)选自如下的谷氨酰胺合成酶抑制剂:双丙氨酰膦(bilanaphos(bialaphos))、双丙氨酰膦(bilanaphos-sodium)、草铵膦和草铵膦(glufosinate-ammonium);
b8)选自如下的DHP合成酶抑制剂:黄草灵(asulam);
b9)选自如下的有丝***抑制剂:胺草磷(amiprophos)、甲基胺草磷(amiprophos-methyl)、氟草胺(benfluralin)、草胺磷(butamiphos)、地乐胺(butralin)、长杀草(carbetamide)、氯苯胺灵(chlorpropham)、敌草索(chlorthal)、敌草索(chlorthal-dimethyl)、敌乐胺(dinitramine)、氟硫草定(dithiopyr)、丁氟消草(ethalfluralin)、氟消草(fluchloralin)、黄草消(oryzalin)、胺硝草(pendimethalin)、氨基丙氟灵(prodiamine)、苯胺灵(propham)、拿草特(propyzamide)、丙戊草胺(tebutam)、噻氟啶草(thiazopyr)和氟乐灵(trifluralin);
b10)选自如下的VLCFA抑制剂:乙草胺(acetochlor)、甲草胺(alachlor)、莎稗磷(anilofos)、丁草胺(butachlor)、唑草胺(cafenstrole)、克草胺(dimethachlor)、噻吩草胺(dimethanamid)、精噻吩草胺(dimethenamid-P)、草乃敌(diphenamid)、四唑酰草胺(fentrazamide)、氟噻草胺(flufenacet)、苯噻草胺(mefenacet)、吡草胺(metazachlor)、异丙甲草胺(metolachlor)、S-异丙甲草胺(metolachlor-S)、萘丙胺(naproanilide)、草萘胺(napropamide)、烯草胺(pethoxamid)、哌草磷(piperophos)、丙草胺(pretilachlor)、扑草胺(propachlor)、异丙草胺(propisochlor)、派罗克杀草砜(pyroxasulfone)(KIH-485)和噻醚草胺(thenylchlor);
式2化合物:
其中各变量具有下列含义:
Y为苯基或如开头所定义的5或6员杂芳基,所述基团可以被1-3个基团Raa取代;
R21、R22、R23、R24为H、卤素或C1-C4烷基;
X为O或NH;
n为0或1。
式2化合物尤其具有下列含义:
其中#表示与该分子的骨架的键;以及
R21、R22、R23、R24各自为H、Cl、F或CH3;
R25为卤素、C1-C4烷基或C1-C4卤代烷基;
R26为C1-C4烷基;
R27为卤素、C1-C4烷氧基或C1-C4卤代烷氧基;
R28为H、卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基;
m为0、1、2或3;
X为氧;
n为0或1。
优选的式2化合物具有下列含义:
R21为H;
R22、R23为F;
R24为H或F;
X为氧;
n为0或1。
特别优选的式2化合物为3-[5-(2,2-二氟乙氧基)-1-甲基-3-三氟甲基-1H-吡唑-4-基甲磺酰基]-4-氟-5,5-二甲基-4,5-二氢异唑(2-1)、3-{[5-(2,2-二氟乙氧基)-1-甲基-3-三氟甲基-1H-吡唑-4-基]氟甲磺酰基}-5,5-二甲基-4,5-二氢异唑(2-2)、4-(4-氟-5,5-二甲基-4,5-二氢异唑-3-磺酰基甲基)-2-甲基-5-三氟甲基-2H-[1,2,3]***(2-3)、4-[(5,5-二甲基-4,5-二氢异唑-3-磺酰基)氟甲基]-2-甲基-5-三氟甲基-2H-[1,2,3]***(2-4)、4-(5,5-二甲基-4,5-二氢异唑-3-磺酰基甲基)-2-甲基-5-三氟甲基-2H-[1,2,3]***(2-5)、3-{[5-(2,2-二氟乙氧基)-1-甲基-3-三氟甲基-1H-吡唑-4-基]二氟甲磺酰基}-5,5-二甲基-4,5-二氢异唑(2-6)、4-[(5,5-二甲基-4,5-二氢异唑-3-磺酰基)二氟甲基]-2-甲基-5-三氟甲基-2H-[1,2,3]***(2-7)、3-{[5-(2,2-二氟乙氧基)-1-甲基-3-三氟甲基-1H-吡唑-4-基]二氟甲磺酰基}-4-氟-5,5-二甲基-4,5-二氢异唑(2-8)、4-[二氟-(4-氟-5,5-二甲基-4,5-二氢异唑-3-磺酰基)甲基]-2-甲基-5-三氟甲基-2H-[1,2,3]***(2-9);
b11)选自如下的纤维素生物合成抑制剂:草克乐(chlorthiamid)、敌草腈(dichlobenil)、胺草唑(flupoxam)和异恶草胺(isoxaben);
b12)选自如下的解偶剂除草剂:地乐酚(dinoseb)、地乐消酚(dinoterb)以及二硝甲酚(DNOC)及其盐;
b13)选自如下的植物生长素除草剂:2,4-D及其盐和酯、2,4-DB及其盐和酯、氨草啶(aminopyralid)及其盐如氨草啶铵盐(aminopyralid-tris(2-hydroxypropyl)ammonium)和其酯、草除灵(benazolin)、草除灵(benazolin-ethyl)、草灭平(chloramben)及其盐和酯、稗草胺(clomeprop)、二氯皮考啉酸(clopyralid)及其盐和酯、麦草畏(dicamba)及其盐和酯、2,4-滴丙酸(dichlorprop)及其盐和酯、高2,4-滴丙酸(dichlorprop-P)及其盐和酯、氟草烟(fluroxypyr)、氟草烟(fluroxypyr-butometyl)、氟氯胺啶(fluroxypyr-meptyl)、MCPA及其盐和酯、2甲4氯乙硫酯(MCPA-thioethyl)、MCPB及其盐和酯、2甲4氯丙酸(mecoprop)及其盐和酯、高2甲4氯丙酸(mecoprop-P)及其盐和酯、毒莠定(picloram)及其盐和酯、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、TBA(2,3,6)及其盐和酯、绿草定(triclopyr)及其盐和酯以及5,6-二氯-2-环丙基-4-嘧啶甲酸(H-9;CAS 858956-08-8)及其盐和酯;
b14)选自如下的植物生长素输送抑制剂:二氟吡隆(diflufenzopyr)、二氟吡隆(diflufenzopyr-sodium)、抑草生(naptalam)和抑草生(naptalam-sodium);
b15)选自如下的其他除草剂:溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、茅草枯、棉隆(dazomet)、苯敌快(difenzoq uat)、苯敌快(difenzoq uat-metilsulfate)、噻节因(dimethipin)、甲胂钠(DSMA)、香草隆(dymron)、敌草腈(endothal)及其盐、乙苯酰草(etobenzanid)、氟燕灵(flamprop)、氟燕灵(flamprop-isopropyl)、甲氟燕灵(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)、抑草丁(flurenol)、抑草丁(flurenol-butyl)、调嘧醇(flurprimidol)、膦铵素(fosamine)、膦铵素(fosamine-ammonium)、茚草酮(indanofan)、抑芽丹(maleic hydrazide)、氟草磺(mefluidide)、威百亩(metam)、叠氮甲烷(methyl azide)、溴甲烷(methyl bromide)、苯丙隆(methyl-dymron)、碘甲烷(methyliodide)、甲胂一钠(MSMA)、油酸(oleic acid)、氯嗪草(oxaziclomefone)、壬酸(pelargonic acid)、稗草畏(pyributicarb)、灭藻醌(quinoclamine)、苯氧丙胺津(triaziflam)、灭草环(tridiphane)和6-氯-3-(2-环丙基-6-甲基苯氧基)-4-哒嗪醇(H-10;CAS 499223-49-3)及其盐和酯。
优选安全剂C的实例为解草酮(benoxacor)、喹氧乙酸(cloquintocet)、抑害腈(cyometrinil)、cyprosulfamide、抑害胺(dichlormid)、dicyclonone、dietholate、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、mephenate、萘二甲酸酐(naphthalic anhydride)、解草腈(oxabetrinil)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(H-11;MON4660,CAS 71526-07-3)和2,2,5-三甲基-3-(二氯乙酰基)-1,3-唑烷(H-12;R-29148,CAS 52836-31-4)。
b1)-b15)组活性化合物和安全剂C是已知的除草剂和安全剂,例如参见The Compendium of Pesticide Common Names(http://www.alanwood.net/pesticides/);B.Hock,C.Fedtke,R.R.Schmidt,Herbizide[除草剂],Georg Thieme Verlag,Stuttgart,1995。其他除草活性化合物由WO96/26202、WO 97/41116、WO 97/41117、WO 97/41118、WO 01/83459和WO 2008/074991,W.等(编辑)"Modern Crop ProtectionCompounds",第1卷,Wiley VCH,2007以及其中引用的文献已知。
本发明还涉及配制成单组分组合物的作物保护组合物形式的组合物,所述单组分组合物包含含有至少一种式I的吡啶化合物和至少一种优选选自b1-b15组活性化合物的其他活性化合物的活性化合物组合以及至少一种固体或液体载体和/或一种或多种表面活性剂和需要的话一种或多种其他常用于作物保护组合物的助剂。
本发明还涉及配制成双组分组合物的作物保护组合物形式的组合物,所述双组分组合物包含含有至少一种式I的吡啶化合物、固体或液体载体和/或一种或多种表面活性剂的第一组分和含有至少一种选自b1-b15组活性化合物的其他活性化合物、固体或液体载体和/或一种或多种表面活性剂的第二组分,其中这两种组分还可以额外包含其他常用于作物保护组合物的助剂。
在包含至少一种式I化合物作为组分A和至少一种除草剂B的二元组合物中,活性化合物A:B的重量比通常为1:1000-1000:1,优选1:500-500:1,尤其是1:250-250:1,特别优选1:75-75:1。
在包含至少一种式I化合物作为组分A和至少一种安全剂C的二元组合物中,活性化合物A:C的重量比通常为1:1000-1000:1,优选1:500-500:1,尤其是1:250-250:1,特别优选1:75-75:1。
在包含至少一种式I化合物作为组分A、至少一种除草剂B和至少一种安全剂C的三元组合物中,组分A:B的相对重量份数通常为1:1000-1000:1,优选1:500-500:1,尤其是1:250-250:1,特别优选1:75-75:1;组分A:C的重量比通常为1:1000-1000:1,优选1:500-500:1,尤其是1:250-250:1,特别优选1:75-75:1;且组分B:C的重量比通常为1:1000-1000:1,优选1:500-500:1,尤其是1:250-250:1,特别优选1:75-75:1。优选组分A+B与组分C的重量比为1:500-500:1,尤其是1:250-250:1,特别优选1:75-75:1。
在每种情况下包含一种单独式I化合物和一种混合配对或混合配对组合的本发明特别优选组合物的实例在下表B中给出。
本发明的另一方面涉及下表B中所列组合物B-1至B-1236,其中在每种情况下表B的一行对应于包含在上述说明中例举的式I化合物之一(组分1)和在每种情况下在所述行中所述的选自b1)-b15)组的其他活性化合物和/或安全剂C(组分2)的除草组合物。所述组合物中的活性化合物在每种情况下优选以协同增效有效量存在。
表B:
本发明化合物I和组合物还可以具有植物增强作用。因此,它们适合调动植物的防御***以对抗不希望的微生物如有害真菌以及病毒和细菌的侵袭。植物增强(诱发抗性)的物质在本发明上下文中应理解为指能够刺激被处理植物的防御***以使得当随后被不希望的微生物接种时被处理植物对这些微生物显示出显著抗性的那些物质。
化合物I可以用于在处理之后的一定时间内保护植物免受不希望的微生物侵袭。起保护作用的时间期限通常为用化合物I处理植物之后或处理种子之后的1-28天,优选1-14天,至多在播种之后9个月。
本发明化合物I和组合物还适合提高收获产量。
此外,它们具有降低的毒性且被植物良好耐受。
下面通过实施例说明式I化合物,本发明主题并不限于所示实施例。
I.合成实施例
适当改变原料,使用下列合成实施例所给程序得到其他化合物I。以此方式得到的化合物与物理数据一起列于下表中。
下面所示产物通过熔点的测定、NMR光谱法或由HPLC-MS光谱法测定的质谱([m/z])或保留时间(RT;[min.])表征。
HPLC-MS=与质谱法联用的高效液相色谱法;HPLC柱:
RP-18柱(来自德国Merck KgaA的Chromolith Speed ROD),50*4.6mm;
移动相:乙腈+0.1%三氟乙酸(TFA)/水+0.1%TFA,在40°C下在5分钟内使用5:95-100:0的梯度,流速:1.8ml/min。
MS:Quadrupole电喷射离子化,80V(正模式)。
Ac:乙酰基;THF:四氢呋喃;DMF:二甲基甲酰胺;dppf:1,1'-二(二苯基膦基)二茂铁;dba:二亚苄基丙酮;PE:石油醚;EtOAc:乙酸乙酯;
DCM:二氯甲烷;NCS:N-氯代琥珀酰亚胺;LiHMDS:六甲基二硅氮烷锂;AcOH:乙酸;MeOH:甲醇;TFA:三氟乙酸;Ph:苯基;i-Pr:异丙基;t-Bu:叔丁基。
实施例1:制备3-[5-氯-3-吗啉代-2-三氟甲基苯基]-4-羟基吡喃并[3,2-b]吡啶-2-酮(下文也称为化合物11,对应于下表I中的化合物I-49)
步骤1:在室温下向化合物1(80g,0.41mol)在800ml AcOH中的溶液中加入Br2(131g,0.82mol)。将该混合物在50°C下搅拌5小时。将该混合物用CH2Cl2稀释并用水、Na2CO3水溶液和盐水洗涤,将有机层在Na2SO4上干燥并真空浓缩,粗产物通过柱层析提纯,得到化合物2(80g,产率:55%)。
1H NMR MeOD 400MHz δ7.69(s,1H)。
步骤2:在-4°C下向化合物2(40g,0.11mol)在H3PO4(1.2L)中的溶液中滴加NaNO2(47g,0.68mol)在200ml水中的溶液,在-4°C下滴加H3PO2(480ml)。将所得混合物在室温下搅拌过夜。将反应混合物用CH2Cl2稀释并用饱和Na2CO3中和,有机层用盐水洗涤,在无水Na2SO4上干燥并真空浓缩,粗产物通过柱层析提纯,得到化合物3(30g,产率:78%)。
1H NMR MeOD 400MHz δ7.93(s,2H)。
步骤3:在N2气氛下将化合物3(10g,29.6mmol)、吗啉(2.6g,29.6mmol)、t-BuONa(5.7g,59.1mmol)、dppf(1.0g,1.77mmol)和Pd2(dba)3(0.81g,0.89mmol)在甲苯(150ml)中的混合物加热至90°C并保持过夜。将反应混合物过滤并真空浓缩,残余物通过柱层析提纯,得到化合物4(2.8g,产率:25%)。
1H NMR MeOD 400MHz δ7.56(s,1H),7.33(s,1H),3.77~3.79(m,4H),2.95~2.97(m,4H)。
步骤4:在N2气氛下将化合物4(5.0g,14.5mmol)、三丁基(氰基甲基)锡烷(5.7g,17.4mmol,对于制备参考J.Org.Chem.1988,53,3051-3057)和PdCl2[(邻甲苯基)3]2(120mg,0.15mmol)在二甲苯(50ml)中的混合物加热至120°C并保持过夜。真空浓缩反应混合物,残余物通过柱层析(PE:EtOAc=10:1)提纯,得到化合物5(1g,产率:24%)。
1H NMR MeOD 400MHz δ7.56(s,1H),7.33(s,1H),4.57(s,2H),3.78~3.80(m,4H),2.95~2.97(m,4H)。
步骤5:将化合物5(2.7g,8.9mmol)在30ml HCl:AcOH(1:1)中的混合物在100°C下搅拌3小时。将反应混合物浓缩并用水稀释,水层用饱和NaHCO3碱化至pH 9并用EtOAc洗涤。将水层酸化至pH 3,用EtOAc萃取并用盐水洗涤。将有机层在无水Na2SO4上干燥并真空浓缩,得到化合物6(1.3g,产率:45%)。
1H NMR:CDCl3400MHz δ7.23(s,1H),7.08(s,1H),3.81~3.83(m,6H),2.89~2.92(m,4H)。
步骤6:在室温下向化合物6(1.3g,4.0mmol)在MeOH(30ml)中的混合物中加入浓H2SO4(0.8g,8.0mmol),然后将所得混合物在回流下加热4小时。真空浓缩反应混合物,用饱和NaHCO3水溶液将残余物碱化并用EtOAc萃取。有机层用盐水洗涤并在Na2SO4上干燥,真空浓缩,得到化合物7(1.1g,产率:81%)。
1H NMR:CDCl3400MHz δ7.23(s,1H),7.08(s,1H),3.95(s,3H),3.81~3.83(m,6H),2.89~2.92(m,4H)。
步骤7:在N2气氛下于-78°C将LiHMDS(0.8mL,0.8mmol,1M)滴加到化合物7(0.34g,0.8mmol)和化合物8(0.3g,0.8mmol)在THF(20mL)中的混合物中。将所得混合物逐渐温热至室温并继续在-78°C下搅拌2小时。将反应混合物用H2O终止并酸化至pH 3,将该混合物用EtOAc萃取并用盐水洗涤,将有机层在无水Na2SO4上干燥并真空浓缩,得到粗化合物9(0.5g,粗),粗产物不经进一步提纯而直接使用。
步骤8:将在TFA(10mL)中的化合物9(0.5g,粗)在室温下搅拌3小时。将反应混合物真空浓缩并通过柱层析(PE:EtOAc=50:1)提纯,得到化合物10(0.1g,产率:20%,来自化合物7)。
步骤9:在室温下向化合物10(0.1g,0.22mmol)在MeOH(6mL)和水(2mL)中的混合物中加入NaOH(35mg,0.87mmol),将所得混合物在室温下搅拌2小时。蒸发反应混合物以除去甲醇,将残余物用水稀释并用EtOAc洗涤,水层用HCl水溶液酸化至pH<3,用DCM萃取。有机层在无水Na2SO4上干燥并真空浓缩,粗产物通过p-HPLC提纯,得到化合物11(30mg,产率:32%)。
1H NMR:CDCl3400MHz δ8.56(d,1H,J=4.4Hz),7.76(d,1H,J=8.8Hz),7.62~7.65(m,1H),7.40(s,1H),7.19(s,1H),4.83(br,1H),3.85~3.87(m,4H),2.97~2.99(m,4H)。
实施例2:制备4-羟基-3-[3-(2-甲氧基乙氧基)-2-三氟甲基苯基]吡喃并[3,2-b]吡啶-2-酮(下文也称为化合物19,对应于下表I中的化合物I-19)
步骤1:向在DMF(10ml)中的2-甲氧基乙醇(1.41g,18.5mol,3当量)中加入氢化钠(800mg,6.1mmol,3当量),在室温下搅拌15分钟,然后将化合物12(1.5g,6.1mmol)加入上述混合物中,在室温下搅拌2小时。将所得溶液用NH4Cl水溶液终止,在EtOAc和水之间分离。在室温下小心浓缩有机溶液。残余物为13(1.6g,88%),其不经进一步提纯而使用。
步骤2:向化合物13(1.5g,5.05mmol)、LiCl(424mg,10.1mmol)和Pd(PPh3)Cl2(353mg,0.505mmol)在10ml DMF中的溶液中,然后将烯丙基三丁基锡烷(2.5g,7.6mmol)加入该反应中,并在N2和90°C下搅拌1小时。该反应用NH4Cl水溶液终止,用EtOAc萃取,将有机层在Na2SO4上干燥,在室温下小心浓缩,得到粗产物14(2.4g,粗),然后直接使用。
1H NMR:CDCl3400MHz δ7.37(t,1H,J=7.6Hz),6.91(d,1H,J=7.6Hz),6.85(d,1H,J=7.6Hz),5.92~5.97(m,1H),5.02~5.06(m,2H),4.18~4.21(m,2H),4.18~4.21(m,2H),3.54~3.56(m,2H),3.45(s,3H)。
步骤3:将粗化合物14(2.4g)在100mL DCM中的溶液冷却至-78°C并用O3鼓泡,直至该溶液变蓝,继续用O3鼓泡0.5小时。将该混合物用氧气和N2吹扫。在0°C下将该冷却溶液滴加入预先制备的琼斯试剂(在冰冷却下向13.4g CrO3在300mL丙酮中的悬浮液中加入10mL浓H2SO4和10mL水)中。将该混合物在室温下搅拌过夜。将反应混合物用i-PrOH终止并过滤。滤液浓缩并用水稀释,碱化至pH 10,用EtOAc洗涤。水相酸化至pH 3,用EtOAc萃取并真空浓缩,得到15(560mg,粗)。
步骤4:向化合物14(560mg,粗)在甲醇(10ml)中的溶液中加入浓H2SO4(352mg,3.6mmol),在回流下搅拌过夜。将所得混合物真空浓缩并用EtOAc/H2O分配,有机层通过盐水洗涤并在Na2SO4上干燥。有机层真空浓缩。残余物通过柱提纯(PE:EtOAc=15:1),得到化合物16(400mg)。
1H NMR:CDCl3400MHz δ7.394(t,1H,J=8Hz),7.003(d,1H,J=8Hz),6.841(d,1H,J=8Hz),4.179(t,2H),3.828(t,2H),3.788(t,2H),3.704(s,3H),3.455(s,3H)。
步骤5:在-78°C和氮气下将LiHMDS(5.5ml,5.5mmol,1M)滴加到化合物8(400mg,1.37mmol)和化合物16(582mg,1.37mmol)在无水THF(50ml)中的溶液中。继续在-78°C下搅拌该混合物,然后温热至室温并搅拌2小时。将该混合物真空浓缩,以黄色糖浆得到化合物17(800mg,粗),其不经进一步提纯而直接使用。
步骤6:在室温下将化合物17(800mg,粗)在TFA(10ml)中的溶液搅拌1小时。用氢氧化钠水溶液将该混合物调节至pH 7。然后不经进一步提纯而将其用于下一步中。
步骤7:在0°C下向化合物18在甲醇/H2O(30ml/10ml)中的溶液中分批加入氢氧化钠(100mg,2.4mmol)。将该混合物室温搅拌1小时。真空除去甲醇。向所得水相中加入水。将其用EtOAc和DCM洗涤。然后将水相调节至pH 3并用DCM萃取3次。将所得有机相在无水硫酸钠上干燥并真空浓缩。残余物通过p-HPLC提纯,以黄色固体得到化合物19(120mg,23%,以三步来自化合物16)。
1H NMR:CDCl3400MHz δ8.545(d,1H,J=8Hz),7.742(d,1H,J=8Hz),7.526~7.61(m,3H),7.140(d,1H,J=8Hz),6.969(d,1H,J=8Hz),4.246(t,2H),3.821(t,2H),3.477(s,3H)。
表I:式I.1A-1化合物
其中Me表示甲基且Ph表示苯基
表II:式I.2A-1化合物
序号 | R1 | R3 | R4 | MS m/z |
II-1 | Cl | H | H | 274.1 |
II-2 | Cl | Cl | H | 385.0 |
II.应用实施例
式I化合物的除草活性通过下列温室试验证实:
所用培养容器为含有含约3.0%腐殖土的壤质砂作为底物的塑料花盆。对每一品种单独播种测试植物的种子。
对于出苗前处理,直接在播种之后借助细分布喷嘴施用悬浮或乳化于水中的活性成分。温和灌溉容器以促进发芽和生长,然后用透明塑料罩覆盖,直到植物生根。该覆盖导致测试植物均匀发芽,除非被活性成分损坏。
对于出苗后处理,首先使测试植物生长到3-15cm的高度,这取决于植物习性,并仅在此时用悬浮或乳化于水中的活性成分处理。为此,将测试植物直接播种并在相同容器中生长,或者首先使它们作为秧苗单独生长并在处理之前几天移植到测试容器中。
取决于品种,将植物保持在10-25°C或20-35°C。测试期为2-4周。在此期间照料植物并评价它们对各处理的响应。
使用0-100的评分进行评价。100表示没有植物出苗,或者至少地面上部分完全受损,而0表示没有损害,或者生长过程正常。对良好的除草活性给予至少70的分值,而对非常好的除草活性给予至少85的分值。
用于温室试验中的植物属于下列品种:
Bayer代码 | 学名 | 英文名 |
ABUTH | Abutilon theophrasti | 苘麻 |
ALOMY | Alopecurus myosuroides | 大穗看麦娘 |
AMARE | Amaranthus retroflexus | 反枝苋 |
Bayer代码 | 学名 | 英文名 |
CHEAL | Chenopodium album | 藜 |
ECHCG | Echinochloa crus-galli | 稗草 |
GALAP | Galium aparine | 猪殃殃 |
SETFA | Setaria faberi | 大狗尾草 |
SETVI | Setaria viridis | 狗尾草 |
在3kg/ha的施用率下,通过出苗后方法施用的化合物II-2对ABUTH显示出非常好的除草活性。
在1kg/ha的施用率下,通过出苗后方法施用的化合物I-4对ALOMY显示出非常好的除草活性。
在0.5kg/ha的施用率下,通过出苗后方法施用的化合物I-9对ALOMY显示出非常好的除草活性。
在0.3kg/ha的施用率下,通过出苗后方法施用的化合物I-22对显示出非常好的除草活性AMARE。
在0.336kg/ha的施用率下,通过出苗后方法施用的化合物I-21对AMARE显示出非常好的除草活性。
在0.5kg/ha的施用率下,通过出苗后方法施用的化合物I-9、I-10、I-16、I-18、I-19、I-20、I-23、I-24、I-27、I-50、I-42、I-43和I-44对AMARE显示出非常好的除草活性。
在0.23kg/ha的施用率下,通过出苗后方法施用的化合物I-30对CHEAL显示出非常好的除草活性。
在0.25kg/ha的施用率下,通过出苗后方法施用的化合物I-12和I-41对CHEAL显示出非常好的除草活性。
在0.336kg/ha的施用率下,通过出苗后方法施用的化合物I-21对CHEAL显示出非常好的除草活性。
在0.5kg/ha的施用率下,通过出苗后方法施用的化合物I-10、I-16、I-18、I-19、I-20、I-23、I-24、I-27、I-38、I-50、I-42、I-43和I-44对CHEAL显示出非常好的除草活性。
在0.177kg/ha的施用率下,通过出苗后方法施用的化合物I-26对ECHCG显示出非常好的除草活性。
在0.5kg/ha的施用率下,通过出苗后方法施用的化合物I-38对ECHCG显示出非常好的除草活性。
在0.25kg/ha的施用率下,通过出苗后方法施用的化合物I-49对GALAP显示出非常好的除草活性。
在1kg/ha的施用率下,通过出苗后方法施用的化合物I-4、II-1和I-25对SETFA显示出非常好的除草活性。
在0.25kg/ha的施用率下,通过出苗后方法施用的化合物I-49对SETVI显示出非常好的除草活性。
Claims (15)
1.式I的取代吡啶或其N-氧化物或可农用盐:
其中各变量具有下列含义:
R为O-RA、S(O)n-RA或O-S(O)n-RA;
RA为氢、C1-C4烷基、Z-C3-C6环烷基、C1-C4卤代烷基、C2-C6链烯基、Z-C3-C6环烯基、C2-C6炔基、Z-(三-C1-C4烷基)甲硅烷基、Z-C(=O)-Ra、Z-NRi-C(O)-NRiRii、Z-P(=O)(Ra)2、NRiRii、3-7员单环或9-10员双环饱和、不饱和或芳族杂环,该杂环含有1、2、3或4个选自O、N和S的杂原子并且可以部分或完全被基团Ra和/或Rb取代,
Ra为氢、OH、C1-C8烷基、C1-C4卤代烷基、Z-C3-C6环烷基、C2-C8链烯基、Z-C5-C6环烯基、C2-C8炔基、Z-C1-C6烷氧基、Z-C1-C4卤代烷氧基、Z-C3-C8链烯氧基、Z-C3-C8炔氧基、NRiRii、C1-C6烷基磺酰基、Z-(三-C1-C4烷基)甲硅烷基、Z-苯基、Z-苯氧基、Z-苯基氨基或含有1、2、3或4个选自O、N和S的杂原子的5-6员单环或9-10员双环杂环,其中环状基团未被取代或者被1、2、3或4个基团Rb取代;
Ri、Rii相互独立地为氢、C1-C8烷基、C1-C4卤代烷基、C3-C8链烯基、C3-C8炔基、Z-C3-C6环烷基、Z-C1-C8烷氧基、Z-C1-C8卤代烷氧基、Z-C(=O)-Ra、Z-苯基、含有1、2、3或4个选自O、N和S的杂原子并且经由Z连接的3-7员单环或9-10员双环饱和、不饱和或芳族杂环;
Ri和Rii与它们所连接的氮原子一起还可以形成含有1、2、3或4个选自O、N和S的杂原子的5-6员单环或9-10员双环杂环;
Z为共价键或C1-C4亚烷基;
n为0、1或2;
R1为氰基、卤素、硝基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6卤代烷基、Z-C1-C6烷氧基、Z-C1-C4烷氧基-C1-C4烷氧基、Z-C1-C4烷硫基、Z-C1-C4烷硫基-C1-C4烷硫基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基、C1-C4卤代烷氧基-C1-C4烷氧基、S(O)nRbb、Z-苯氧基、Z-杂环氧基,其中杂环基为含有1、2、3或4个选自O、N和S的杂原子的5-6员单环或9-10员双环饱和、部分不饱和或芳族杂环,其中环状基团未被取代或者部分或完全被Rb取代;
Rbb为C1-C8烷基、C2-C6链烯基、C2-C6炔基、C2-C6卤代链烯基、C2-C6卤代炔基或C1-C6卤代烷基且n为0、1或2;
A为N或C-R2;
R2为Z1-苯基、苯氧基或Z1-杂环基,其中杂环基为含有1、2、3或4个选自O、N和S的杂原子的5-6员单环或9-10员双环饱和、部分不饱和或芳族杂环,其中环状基团未被取代或者部分或完全被Rb取代;
C1-C8烷基、C2-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基、C2-C8链烯基、C2-C8炔基、C2-C8卤代链烯基、C2-C8卤代炔基、C2-C6烷氧基、Z-C1-C4烷氧基-C1-C4烷氧基、Z-C1-C4卤代烷氧基-C1-C4烷氧基、C2-C6卤代烷氧基、C3-C6链烯氧基、C3-C6炔氧基、C2-C6烷硫基、C2-C6卤代烷硫基、Z-C(=O)-Ra、S(O)1-2Rbb;
Z1为共价键、C1-C4亚烷氧基、C1-C4氧亚烷基或C1-C4亚烷氧基-C1-C4亚烷基;
Rb相互独立地为Z-CN、Z-OH、Z-NO2、Z-卤素、氧代(=O)、=N-Ra、C1-C8烷基、C1-C4卤代烷基、C2-C8链烯基、C2-C8炔基、Z-C1-C8烷氧基、Z-C1-C8卤代烷氧基、Z-C3-C10环烷基、O-Z-C3-C10环烷基、Z-C(=O)-Ra、NRiRii、Z-(三-C1-C4烷基)甲硅烷基、Z-苯基和S(O)nRbb;两个基团Rb可以一起形成具有3-6个环成员且除了碳原子外还可以含有选自O、N和S的杂原子以及可以未被取代或者被其他基团Rb取代的环;
R2与相邻碳原子所连接的基团一起还可以形成除了碳原子外还可以含有1、2或3个选自O、N和S的杂原子并且可以被其他基团Rb取代的5-10员饱和或部分或完全不饱和单环或双环;
R3为氢、卤素、氰基、硝基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C4链烯基、C2-C4炔基、C2-C4链烯氧基、C2-C4炔氧基、S(O)nRbb;
R4为氢、卤素或C1-C4卤代烷基;
R5为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷氧基、C1-C4卤代烷硫基;
R6、R7相互独立地为氢、卤素或C1-C4烷基;
Y为O或S;
X为O、S或N-Rx;
Rx为氢、C1-C6烷基、C1-C4卤代烷基、C2-C6链烯基、C3-C6炔基、Z-C3-C10环烷基、C1-C6烷氧基-C1-C6烷基、C1-C6氰基烷基、Z-苯基、Z-C(=O)-Ra2或三-C1-C4烷基甲硅烷基;
Ra2为C1-C6烷基、C1-C4卤代烷基、Z-C1-C6烷氧基、Z-C1-C4卤代烷氧基或NRiRii;
其中在基团RA及其子取代基中,碳链和/或环状基团可以部分或完全被基团Rb取代。
2.根据权利要求1的式I化合物,其中A为CR2。
3.根据权利要求2的式I化合物,其中R2为含有1、2、3或4个选自O、N和S的杂原子的任选取代的5或6员饱和、部分不饱和或芳族杂环。
6.根据权利要求5的式I化合物,其中基团Rb选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基和C1-C4烷硫基-C1-C4烷基。
7.根据权利要求2的式I化合物,其中R2为选自C1-C6烷基、C1-C4烷氧基-C1-C4烷基、C1-C4卤代烷氧基-C1-C4烷基、C2-C6链烯基、C2-C6炔基、C2-C4烷氧基、C2-C4卤代烷氧基、C3-C6链烯氧基、C3-C6炔氧基、C3-C6卤代链烯氧基、C3-C6卤代炔氧基、C1-C4烷氧羰基、S(O)2-C1-C8烷基和S(O)2-C1-C8卤代烷基的脂族基团。
8.根据权利要求1-7中任一项的式I化合物,其中
R1为卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基或C1-C4烷基磺酰基;以及
R3为H、卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基。
9.根据权利要求2的式I化合物,其中R2与R1或R3一起形成任选被Rb取代的含有1、2、3或4个选自O、N和S的杂原子的5-10员部分不饱和单环或双环。
11.根据权利要求1的式I化合物,其中A为N。
12.根据权利要求11的式I化合物,其中
R1为硝基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基或C1-C4烷基磺酰基;和
R3为H、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基或C1-C4烷基磺酰基。
13.根据权利要求1-12中任一项的式I化合物,其中X、Y相互独立地为O或S且R4、R5、R6、R7为H。
14.一种包含除草有效量的至少一种根据权利要求1-13中任一项的式I化合物或其可农用盐以及常用于配制作物保护剂的助剂的组合物。
15.一种防止不希望的植物生长的方法,包括使除草有效量的至少一种根据权利要求1-13中任一项的式I化合物或其可农用盐作用于植物、其种子和/或其生长地。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105875625A (zh) * | 2015-02-12 | 2016-08-24 | 龙灯农业化工国际有限公司 | 制备新颖的砜嘧磺隆制剂的方法及其用途 |
CN107531673A (zh) * | 2015-04-30 | 2018-01-02 | 先正达参股股份有限公司 | 除草化合物 |
CN107567455A (zh) * | 2015-04-30 | 2018-01-09 | 先正达参股股份有限公司 | 除草化合物 |
CN107580599A (zh) * | 2015-04-30 | 2018-01-12 | 先正达参股股份有限公司 | 除草化合物 |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR081526A1 (es) | 2010-03-23 | 2012-10-03 | Basf Se | Piridazinas sustituidas que tienen accion herbicida |
US8575068B2 (en) | 2010-03-23 | 2013-11-05 | Basf Se | Pyrazinothiazines having herbicidal action |
EA201201322A1 (ru) | 2010-03-23 | 2013-05-30 | Басф Се | Пиридотиазины, обладающие гербицидным действием |
EA022263B1 (ru) | 2010-07-22 | 2015-11-30 | Басф Се | Гербицидные изоксазоло[5,4-в]пиридины |
IN2014CN04204A (zh) | 2012-01-12 | 2015-07-17 | Basf Se | |
US10294488B2 (en) | 2012-12-18 | 2019-05-21 | Basf Se | Herbicide-metabolizing cytochrome P450 monooxygenases |
AU2014209278B2 (en) * | 2013-01-25 | 2017-06-15 | Corteva Agriscience Llc | Selective weed control methods |
WO2016174073A1 (en) * | 2015-04-30 | 2016-11-03 | Syngenta Participations Ag | Herbicidal compounds |
EP3133065A1 (en) | 2015-08-21 | 2017-02-22 | Merck Patent GmbH | Compounds for optically active devices |
US10573722B2 (en) * | 2016-02-17 | 2020-02-25 | General Electric Company | Systems and methods for in-situ doped semiconductor gate electrodes for wide bandgap semiconductor power devices |
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EP3363786A1 (en) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Compounds for optically active devices |
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WO2021233800A1 (en) | 2020-05-20 | 2021-11-25 | Merck Patent Gmbh | Azacoumarin and azathiocoumarin derivatives for use in optically active devices |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5801183A (en) * | 1995-01-27 | 1998-09-01 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Aza and aza (N-oxy) analogs of glycine/NMDA receptor antagonists |
CN1826341A (zh) * | 2003-07-18 | 2006-08-30 | 巴斯福股份公司 | 芳基稠合的3-芳基吡啶化合物及其在防治病原性真菌中的用途 |
WO2009090401A2 (en) * | 2008-01-17 | 2009-07-23 | Syngenta Limited | Herbicidal compounds |
WO2010049270A1 (de) * | 2008-10-29 | 2010-05-06 | Basf Se | Substituierte pyridine mit herbizider wirkung |
Family Cites Families (58)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5304732A (en) | 1984-03-06 | 1994-04-19 | Mgi Pharma, Inc. | Herbicide resistance in plants |
BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
EP0242236B2 (en) | 1986-03-11 | 1996-08-21 | Plant Genetic Systems N.V. | Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering |
US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
IL83348A (en) | 1986-08-26 | 1995-12-08 | Du Pont | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
FR2629098B1 (fr) | 1988-03-23 | 1990-08-10 | Rhone Poulenc Agrochimie | Gene chimerique de resistance herbicide |
US4986845A (en) | 1988-07-15 | 1991-01-22 | Nissan Chemical Industries Ltd. | Pyrazole derivatives and herbicides containing them |
EP0374753A3 (de) | 1988-12-19 | 1991-05-29 | American Cyanamid Company | Insektizide Toxine, Gene, die diese Toxine kodieren, Antikörper, die sie binden, sowie transgene Pflanzenzellen und transgene Pflanzen, die diese Toxine exprimieren |
US6689356B1 (en) | 1988-12-19 | 2004-02-10 | The Regents Of The Unviersity Of California | Recombinant baculoviruses producing insect toxins |
EP0392225B1 (en) | 1989-03-24 | 2003-05-28 | Syngenta Participations AG | Disease-resistant transgenic plants |
ATE121267T1 (de) | 1989-11-07 | 1995-05-15 | Pioneer Hi Bred Int | Larven abtötende lektine und darauf beruhende pflanzenresistenz gegen insekten. |
ES2173077T3 (es) | 1990-06-25 | 2002-10-16 | Monsanto Technology Llc | Plantas que toleran glifosato. |
UA48104C2 (uk) | 1991-10-04 | 2002-08-15 | Новартіс Аг | Фрагмент днк, який містить послідовність,що кодує інсектицидний протеїн, оптимізовану для кукурудзи,фрагмент днк, який забезпечує направлену бажану для серцевини стебла експресію зв'язаного з нею структурного гена в рослині, фрагмент днк, який забезпечує специфічну для пилку експресію зв`язаного з нею структурного гена в рослині, рекомбінантна молекула днк, спосіб одержання оптимізованої для кукурудзи кодуючої послідовності інсектицидного протеїну, спосіб захисту рослин кукурудзи щонайменше від однієї комахи-шкідника |
US5530195A (en) | 1994-06-10 | 1996-06-25 | Ciba-Geigy Corporation | Bacillus thuringiensis gene encoding a toxin active against insects |
DE19505995A1 (de) | 1995-02-21 | 1996-08-22 | Degussa | Verfahren zur Herstellung von Thietanonen |
US5846906A (en) | 1995-02-24 | 1998-12-08 | Basf Aktiengesellschaft | Herbicidally active phenyldiketone compounds |
PL328505A1 (en) | 1996-02-24 | 1999-02-01 | Basf Ag | 2-heteroaroylcyclohexano-1,3-diones |
AU1670797A (en) | 1996-04-26 | 1997-11-19 | Nippon Soda Co., Ltd. | Benzene derivatives substituted by heterocycles and herbicides |
AU1670997A (en) | 1996-04-26 | 1997-11-19 | Nippon Soda Co., Ltd. | Novel benzene derivatives substituted by heterocycles and herbicides |
CN1076351C (zh) | 1996-04-26 | 2001-12-19 | 日本曹达株式会社 | 被杂环取代的苯的衍生物和除草剂 |
US5773704A (en) | 1996-04-29 | 1998-06-30 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Herbicide resistant rice |
US5773702A (en) | 1996-07-17 | 1998-06-30 | Board Of Trustees Operating Michigan State University | Imidazolinone herbicide resistant sugar beet plants |
EP0960190B1 (en) | 1996-07-17 | 2006-10-18 | Michigan State University | Imidazolinone herbicide resistant sugar beet plants |
DE19638486A1 (de) | 1996-09-20 | 1998-03-26 | Basf Ag | Hetaroylderivate |
US6010981A (en) | 1997-05-23 | 2000-01-04 | Dow Agrosciences Llc | 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides |
US6348643B1 (en) | 1998-10-29 | 2002-02-19 | American Cyanamid Company | DNA sequences encoding the arabidopsis acetohydroxy-acid synthase small subunit and methods of use |
AU2001259206B2 (en) | 2000-04-28 | 2006-05-25 | Basf Aktiengesellschaft | Use of the maize x112 mutant ahas 2 gene and imidazolinone herbicides for selection of transgenic monocots, maize, rice and wheat plants resistant to the imidazolinone herbicides |
EA005677B1 (ru) | 2000-05-04 | 2005-04-28 | Басф Акциенгезельшафт | Гетероциклилзамещенные фенилсульфамоилкарбоксамиды |
CN1210269C (zh) | 2000-07-17 | 2005-07-13 | 巴斯福股份公司 | 4-硫烷基溴苯衍生物的制备 |
ES2243543T3 (es) | 2000-08-25 | 2005-12-01 | Syngenta Participations Ag | Hibridos de proteinas cristalinas de bacillus thurigiensis. |
WO2003014357A1 (en) | 2001-08-09 | 2003-02-20 | University Of Saskatchewan | Wheat plants having increased resistance to imidazolinone herbicides |
US7528297B2 (en) | 2001-08-09 | 2009-05-05 | Northwest Plant Breeding Company | Wheat plants having increased resistance to imidazolinone herbicides |
CA2456311C (en) | 2001-08-09 | 2014-04-08 | University Of Saskatchewan | Wheat plants having increased resistance to imidazolinone herbicides |
US7230167B2 (en) | 2001-08-31 | 2007-06-12 | Syngenta Participations Ag | Modified Cry3A toxins and nucleic acid sequences coding therefor |
AR037856A1 (es) | 2001-12-17 | 2004-12-09 | Syngenta Participations Ag | Evento de maiz |
EP1551218B1 (en) | 2002-07-10 | 2017-05-17 | The Department of Agriculture, Western Australia | Wheat plants having increased resistance to imidazolinone herbicides |
US6870067B2 (en) | 2002-10-08 | 2005-03-22 | Merck & Co., Inc. | Process for the synthesis of trifluorophenylacetic acids |
US20040068141A1 (en) | 2002-10-08 | 2004-04-08 | Armstrong Joseph D. | Process for the synthesis of trifluorophenylacetic acids |
MXPA05012733A (es) | 2003-05-28 | 2006-05-17 | Basf Ag | Plantas de trigo que tienen tolerancia incrementada a los herbicidas de imidazolinona. |
AR047107A1 (es) | 2003-08-29 | 2006-01-11 | Inst Nac De Tecnologia Agropec | Plantas de arroz que tienen una mayor tolerancia a los herbicidas de imidazolinona |
GB0614471D0 (en) | 2006-07-20 | 2006-08-30 | Syngenta Ltd | Herbicidal Compounds |
GB0624760D0 (en) | 2006-12-12 | 2007-01-17 | Syngenta Ltd | Herbicidal compounds |
GB0625598D0 (en) | 2006-12-21 | 2007-01-31 | Syngenta Ltd | Novel herbicides |
AU2008319418B2 (en) | 2007-10-29 | 2013-08-15 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
GB0722472D0 (en) | 2007-11-15 | 2007-12-27 | Syngenta Ltd | Herbicidal compounds |
GB0800856D0 (en) | 2008-01-17 | 2008-02-27 | Syngenta Ltd | Herbicidal compounds |
GB0816880D0 (en) | 2008-09-15 | 2008-10-22 | Syngenta Ltd | Improvements in or relating to organic compounds |
WO2010069802A1 (de) | 2008-12-18 | 2010-06-24 | Basf Se | Heterozyklische diketon-derivate mit herbizider wirkung |
JP2012528821A (ja) | 2009-06-05 | 2012-11-15 | ビーエーエスエフ ソシエタス・ヨーロピア | 除草活性を有する置換されたピラジン(チオ)ピラン類 |
WO2011051212A1 (de) | 2009-10-28 | 2011-05-05 | Basf Se | Verwendung heteroaromatischer verbindungen als herbizide |
US8329619B2 (en) | 2009-11-03 | 2012-12-11 | Basf Se | Substituted quinolinones having herbicidal action |
WO2011057989A1 (en) | 2009-11-11 | 2011-05-19 | Basf Se | Heterocyclic compounds having herbicidal action |
WO2011058036A1 (en) | 2009-11-13 | 2011-05-19 | Basf Se | Tricyclic compounds having herbicidal action |
EA201201322A1 (ru) | 2010-03-23 | 2013-05-30 | Басф Се | Пиридотиазины, обладающие гербицидным действием |
CN102812024B (zh) | 2010-03-23 | 2015-01-21 | 巴斯夫欧洲公司 | 具有除草作用的取代吡啶 |
US8575068B2 (en) | 2010-03-23 | 2013-11-05 | Basf Se | Pyrazinothiazines having herbicidal action |
BR112012023935A2 (pt) | 2010-03-23 | 2015-09-15 | Basf Se | piridazina substituída da fórmula i, composto para fórmula i, composição e método para o controle de vegetação indesejada |
AR081526A1 (es) | 2010-03-23 | 2012-10-03 | Basf Se | Piridazinas sustituidas que tienen accion herbicida |
-
2011
- 2011-03-21 US US13/636,430 patent/US8809535B2/en not_active Expired - Fee Related
- 2011-03-21 EP EP11708891A patent/EP2550276A1/en not_active Withdrawn
- 2011-03-21 CN CN2011800246379A patent/CN102906096A/zh active Pending
- 2011-03-21 BR BR112012023765A patent/BR112012023765A2/pt not_active IP Right Cessation
- 2011-03-21 JP JP2013500454A patent/JP2013522339A/ja not_active Withdrawn
- 2011-03-21 WO PCT/EP2011/054258 patent/WO2011117195A1/en active Application Filing
- 2011-03-22 AR ARP110100937A patent/AR081319A1/es unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5801183A (en) * | 1995-01-27 | 1998-09-01 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Aza and aza (N-oxy) analogs of glycine/NMDA receptor antagonists |
CN1826341A (zh) * | 2003-07-18 | 2006-08-30 | 巴斯福股份公司 | 芳基稠合的3-芳基吡啶化合物及其在防治病原性真菌中的用途 |
WO2009090401A2 (en) * | 2008-01-17 | 2009-07-23 | Syngenta Limited | Herbicidal compounds |
WO2010049270A1 (de) * | 2008-10-29 | 2010-05-06 | Basf Se | Substituierte pyridine mit herbizider wirkung |
Non-Patent Citations (2)
Title |
---|
KELLY FRAZIER,等: "Design and structure–activity relationship of heterocyclic analogs of 4-amino-3-benzimidazol-2-ylhydroquinolin-2-ones as inhibitors of receptor tyrosine kinases", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》, vol. 16, no. 8, 15 April 2006 (2006-04-15), pages 2247 - 2251, XP002557592, DOI: doi:10.1016/j.bmcl.2006.01.020 * |
ZHANG-LIN ZHOU,等: "Synthesis and SAR of 5-, 6-, 7- and 8-Aza Analogues of 3-Aryl-4-hydroxyquinolin-2(1H)-one as NMDA/Glycine Site Antagonists", 《BIOORGANIC & MEDICINAL CHEMISTRY》, vol. 9, no. 8, 31 August 2001 (2001-08-31), pages 2061 - 2071, XP002557591, DOI: doi:10.1016/S0968-0896(01)00115-8 * |
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CN105875625B (zh) * | 2015-02-12 | 2020-12-08 | 龙灯农业化工国际有限公司 | 制备砜嘧磺隆制剂的方法及其用途 |
CN107531673A (zh) * | 2015-04-30 | 2018-01-02 | 先正达参股股份有限公司 | 除草化合物 |
CN107567455A (zh) * | 2015-04-30 | 2018-01-09 | 先正达参股股份有限公司 | 除草化合物 |
CN107580599A (zh) * | 2015-04-30 | 2018-01-12 | 先正达参股股份有限公司 | 除草化合物 |
CN111484509A (zh) * | 2015-04-30 | 2020-08-04 | 先正达参股股份有限公司 | 除草化合物 |
CN107580599B (zh) * | 2015-04-30 | 2020-11-03 | 先正达参股股份有限公司 | 除草化合物 |
CN107531673B (zh) * | 2015-04-30 | 2020-12-08 | 先正达参股股份有限公司 | 除草化合物 |
Also Published As
Publication number | Publication date |
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WO2011117195A1 (en) | 2011-09-29 |
BR112012023765A2 (pt) | 2015-09-29 |
JP2013522339A (ja) | 2013-06-13 |
US8809535B2 (en) | 2014-08-19 |
US20130023415A1 (en) | 2013-01-24 |
EP2550276A1 (en) | 2013-01-30 |
AR081319A1 (es) | 2012-08-08 |
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