CN111868034A - 作为除草剂的螺环环己二酮衍生物 - Google Patents
作为除草剂的螺环环己二酮衍生物 Download PDFInfo
- Publication number
- CN111868034A CN111868034A CN201980018862.8A CN201980018862A CN111868034A CN 111868034 A CN111868034 A CN 111868034A CN 201980018862 A CN201980018862 A CN 201980018862A CN 111868034 A CN111868034 A CN 111868034A
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- China
- Prior art keywords
- alkyl
- group
- radical
- phenyl
- haloalkyl
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims description 15
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical class O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 241000196324 Embryophyta Species 0.000 claims abstract description 29
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 21
- -1 C2-C6Alkenyl radical Chemical class 0.000 claims description 83
- 150000003254 radicals Chemical class 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 239000000575 pesticide Substances 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 244000045561 useful plants Species 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000000843 powder Substances 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- 229910052740 iodine Inorganic materials 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229910052763 palladium Inorganic materials 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000004530 micro-emulsion Substances 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 244000038559 crop plants Species 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 5
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000004546 suspension concentrate Substances 0.000 description 5
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- YHKBGVDUSSWOAB-UHFFFAOYSA-N 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(CC(Cl)C(O)=O)=C(Cl)C=C1F YHKBGVDUSSWOAB-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 4
- 239000004491 dispersible concentrate Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000010353 genetic engineering Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000003053 toxin Substances 0.000 description 4
- 231100000765 toxin Toxicity 0.000 description 4
- 108700012359 toxins Proteins 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- NQGUUWYZWAWOIX-UHFFFAOYSA-N 1-(1-methoxypiperidin-4-ylidene)propan-2-one Chemical compound CON1CCC(CC1)=CC(C)=O NQGUUWYZWAWOIX-UHFFFAOYSA-N 0.000 description 3
- CUJMCPPBTUATEJ-UHFFFAOYSA-N 1-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)ethanone Chemical compound C1=CC=C2[N+](=O)C(C(=O)C)=C(C)N([O-])C2=C1 CUJMCPPBTUATEJ-UHFFFAOYSA-N 0.000 description 3
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 3
- GLKNCNPFGVUCOE-UHFFFAOYSA-N 3-acetyl-9-[4-(5-fluoropyrimidin-2-yl)-2,6-dimethylphenyl]-3-azaspiro[5.5]undecane-8,10-dione Chemical compound C(C)(=O)N1CCC2(CC1)CC(C(C(C2)=O)C1=C(C=C(C=C1C)C1=NC=C(C=N1)F)C)=O GLKNCNPFGVUCOE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241001621841 Alopecurus myosuroides Species 0.000 description 3
- 239000005476 Bentazone Substances 0.000 description 3
- 235000006008 Brassica napus var napus Nutrition 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 241000400611 Eucalyptus deanei Species 0.000 description 3
- 239000005561 Glufosinate Substances 0.000 description 3
- 239000005562 Glyphosate Substances 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 240000004296 Lolium perenne Species 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000005602 Propyzamide Substances 0.000 description 3
- 239000005603 Prosulfocarb Substances 0.000 description 3
- 239000005605 Pyraflufen-ethyl Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 3
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 238000009395 breeding Methods 0.000 description 3
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- 238000001816 cooling Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
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- 239000011777 magnesium Substances 0.000 description 3
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 3
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 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 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 241000894007 species Species 0.000 description 3
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- 230000009261 transgenic effect Effects 0.000 description 3
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
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- XEJNEDVTJPXRSM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C1(C)CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl XEJNEDVTJPXRSM-UHFFFAOYSA-N 0.000 description 2
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical class [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 description 2
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Abstract
本发明涉及具有式(I)的化合物,其中R1、R2、R3、R4和G是如本文所定义。本发明进一步涉及包含具有式(I)的化合物的除草组合物、其用于特别是在有用植物的作物中控制杂草的用途。
Description
本发明涉及新颖的除草环己二酮化合物、其制备方法、包含所述新颖的化合物的除草组合物、以及其用于控制杂草的用途。
例如在WO 2008/110308中披露了被具有各种取代基的苯基取代的除草环状二酮化合物。本发明涉及新颖的具有改进特性的除草环己二酮衍生物。
因此,根据本发明,提供了一种具有式(I)的化合物
其中
R1选自甲基、苯基和包含一个或两个氮杂原子的5元或6元杂芳基,所述苯基和杂芳基任选地被一个或两个R15取代基取代;
R2是甲基或甲氧基;
R3是甲基或甲氧基;
R4选自由以下组成的组:C1-C4烷基、C1-C4烷氧基-、C1-C4卤代烷基、-C(=O)C1-C4烷基、-C(=O)C1-C4卤代烷基、-S(O)nC1-C6烷基、-S(O)nC1-C6卤代烷基、-S(O)n-(CH2)n-C3-C6环烷基、-S(O)nC(R11)R12R13、-C(O)H、-C(O)-(CH2)n-C3-C6环烷基、-C(O)C(R11)R12R13、-C(O)C2-C4烯基、-C(O)(CR9R10)CN、-C(O)(CR9R10)(CR9R10)CN、-C(O)CH2C(O)-C1-C6烷基、-C(O)CH2OC(O)-C1-C6烷基、-C(O)OC1-C6烷基、-C(O)OC1-C6卤代烷基、-C(O)(R9R10)nS(O)nC1-C6烷基、-C(O)C1-C3烷氧基C1-C6烷基、-C(O)C1-C3烷氧基C2-C6烯基、-C(O)C1-C3烷氧基C2-C6炔基、-C(O)C1-C3烷氧基C1-C6卤代烷基、-C(O)C1-C3烷氧基C3-C6环烷基、-C(O)OC1-C3烷氧基C1-C6烷基、-C(O)C1-C3烷氧基C1-C3烷氧基C1-C6烷基、-C(O)(CH2)nNR5R6、-C(O)-(CH2)n-NR7C(O)R8、-C(O)-(CH2)n-O-N=CR5R5、-CN、-(CH2)n-苯基、-C(O)-(CH2)n-苯基、-S(O)n-(CH2)n-苯基、-杂环基、-C(O)-(CH2)n-杂环基、-C(O)(CH2)nO-(CH2)n-杂环基、-S(O)n-(CH2)n-杂环基,其中每个杂环基是5元或6元杂环基,所述杂环基可以是芳香族的、饱和的或部分饱和的并且可以含有从1至4个各自独立地选自由氧、氮和硫组成的组的杂原子,并且其中所述杂环基或苯基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
R5选自由氢和C1-C6烷基组成的组;
R6选自由以下组成的组:氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、羟基-、C1-C6烷氧基、C3-C6环烷基、-C1-C4烷氧基C1-C6烷基、-C1-C3烷氧基C1-C6卤代烷基、-(CR9R10)C1-C6卤代烷基、-(CR9R10)C(O)NR5R5、苯基、-吡啶基,其中所述苯基和吡啶基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;或者
R5和R6一起形成-CH2CH2OCH2CH2-;并且
R7选自由氢和C1-C6烷基组成的组;
R8选自由以下组成的组:氢、C1-C6烷基、C1-C6烷氧基、C3-C6环烷基、苯基、-吡啶基,其中所述苯基和吡啶基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
R9是氢或甲基;
R10是氢或甲基;或者
R9和R10一起形成-CH2CH2-;并且
R11是氢或甲基;
R12选自由以下组成的组:氢、C1-C6烷基、羟基和C1-C6烷氧基-;
R13选自由以下组成的组:氢、C1-C6烷基、羟基和C1-C6烷氧基;或者
R12和R13一起形成-CH2-X-CH2-;并且
X选自由O、S和N-R14组成的组;
R14选自由以下组成的组:氢、C1-C3烷基和C1-C3烷氧基-;
R15独立地选自由以下组成的组:C1-C4烷基、C1-C4卤代烷基、氰基和卤素;
G选自由以下组成的组:氢、-(CH2)n-Ra、-C(O)-Ra、-C(O)-(CRcRd)n-O-Rb、-C(O)-(CRcRd)n-S-Rb、-C(O)NRaRa、-S(O)2-Ra和C1-C8烷氧基-C1-C3烷基-;
Ra独立地选自由以下组成的组:氢、C1-C8烷基、C1-C3卤代烷基、C2-C8烯基、C2-C8炔基、C3-C6环烷基、杂环基和苯基,其中所述杂环基和苯基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
Rb选自由以下组成的组:C1-C8烷基、C1-C3卤代烷基、C2-C8烯基、C2-C8炔基、C3-C6环烷基、杂环基和苯基,其中所述杂环基和苯基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
Rc是氢或C1-C3烷基;
Rd是氢或C1-C3烷基;并且
n独立地是0、1或2;
或其农业上可接受的盐。
烷基(例如C1-C6烷基)包括例如甲基(Me,CH3)、乙基(Et,C2H5)、正丙基(n-Pr)、异丙基(i-Pr)、正丁基(n-Bu)、异丁基(i-Bu)、仲丁基(s-Bu)和叔丁基(t-Bu)。
烯基与炔基部分可以处于直链或支链的形式,并且这些烯基部分适当时可以是具有(E)-或(Z)-构型。实例是乙烯基、烯丙基以及炔丙基。烯基和炔基部分可以以任何组合含有一个或多个双键和/或三键。
卤素(或卤代)涵盖了氟、氯、溴或碘。所述卤素(或卤代)对应地应用于其他定义背景下的卤素,如卤代烷基。
卤代烷基(例如C1-C6卤代烷基)是例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基和2,2,2-三氯乙基、七氟正丙基和全氟正己基。
烷氧基(例如C1-C4烷氧基-)是例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基,优选甲氧基和乙氧基。
烷氧基烷基(例如C1-C8烷氧基-C1-C3烷基-)包括例如甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、正丙氧基甲基、正丙氧基乙基、异丙氧基甲基或异丙氧基乙基。
环烷基(例如C3-C6环烷基-)包括例如环丙基(c-丙基,c-Pr)、环丁基(c-丁基、c-Bu)、环戊基(c-戊基)和环己基(c-己基)并且如所指出的可以是取代的或未取代的。
C1-C6烷基-S-(烷硫基)是,例如甲硫基、乙硫基、丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基,优选地是甲硫基或乙硫基。
C1-C6烷基-S(O)-(烷基亚磺酰基)是,例如甲基亚磺酰基、乙基亚磺酰基、丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基或叔丁基亚磺酰基,优选甲基亚磺酰基或乙基亚磺酰基。
C1-C6烷基-S(O)2-(烷基磺酰基)是,例如甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基或叔丁基磺酰基,优选甲基磺酰基或乙基磺酰基。
杂环基,除非另有说明,否则是5元或6元杂环基,其可以是芳香族的、饱和的或部分饱和的并且可以含有从1至4个各自独立地选自由氧、氮和硫组成的组的杂原子。
本发明还涉及具有式(I)的化合物的农业上可接受的盐。此类盐包括能够与胺、碱金属和碱土金属碱或者季铵碱形成的那些。在作为成盐物的碱金属以及碱土金属氢氧化物之中,应特别提及锂、钠、钾、镁以及钙的氢氧化物,但尤其是钠和钾的氢氧化物。根据本发明的具有式(I)的化合物还包括在盐形成期间可以形成的水合物。
适合于形成铵盐的胺的实例包括氨以及伯、仲和叔C1-C18烷基胺,C1-C4羟基烷基胺以及C2-C4烷氧基烷基胺,例如甲胺、乙胺、正丙胺、异丙胺、四种丁胺异构体、正戊胺、异戊胺、己胺、庚胺、辛胺、壬胺、癸胺、十五胺、十六胺、十七胺、十八胺、甲基乙基胺、甲基异丙胺、甲基己胺、甲基壬胺、甲基十五胺、甲基十八胺、乙基丁胺、乙基庚胺、乙基辛胺、己基庚胺、己基辛胺、二甲胺、二乙胺、二-正丙胺、二异丙胺、二-正丁胺、二-正戊胺、二异戊胺、二己胺、二庚胺、二辛胺、乙醇胺、正丙醇胺、异丙醇胺、N,N-二乙醇胺、N-乙基丙醇胺、N-丁基乙醇胺、烯丙胺、正-丁-2-烯胺、正戊-2-烯胺、2,3-二甲基丁-2-烯胺、二丁-2-烯胺、正己-2-烯胺、丙二胺、三甲胺、三乙胺、三-正丙胺、三异丙胺、三-正丁胺、三异丁胺、三-仲丁胺、三-正戊胺、甲氧基乙基胺以及乙氧基乙基胺;杂环胺,例如吡啶、喹啉、异喹啉、吗啉、哌啶、吡咯烷、二氢吲哚、奎宁环以及氮杂卓;伯芳基胺,例如苯胺,甲氧基苯胺,乙氧基苯胺,邻-、间-和对-甲苯胺,苯二胺,联苯胺,萘胺以及邻-、间-和对-氯苯胺;但尤其是三乙胺、异丙胺和二异丙胺。
在本发明的一个实施例中,R1是甲基。
在本发明的另一个实施例中,R1是任选地被一个或两个R15取代基取代的苯基,所述R15取代基例如选自由以下组成的组:氰基、氯和氟。
在本发明的另一个实施例中,R1是包含一个或两个氮杂原子的5元或6元杂芳基,所述杂芳基任选地被一个或两个R15取代基取代,所述R15取代基例如选自由以下组成的组:氰基、氯和氟。在优选的实施例中,所述杂芳基选自由以下组成的组:吡啶基、嘧啶基和吡唑基。
在本发明的一个实施例中,R2是甲基。
在本发明的一个实施例中,R3是甲基。
在本发明的另一个实施例中,R3是甲氧基。
在本发明的一个实施例中,R2是甲基并且R3是甲基。
在本发明的一个实施例中,R2是甲基并且R3是甲氧基。
在本发明的一个实施例中,R2是甲氧基并且R3是甲氧基。
在本发明的一个实施例中,R4选自由以下组成的组:C1-C4烷基、C1-C4烷氧基-、C1-C4卤代烷基、-C(=O)C1-C4烷基、-C(=O)C1-C4卤代烷基、-S(O)nC1-C6烷基、-S(O)nC1-C6卤代烷基、-S(O)n-(CH2)n-C3-C6环烷基、-S(O)nC(R11)R12R13、-C(O)H、-C(O)-(CH2)n-C3-C6环烷基、-C(O)C(R11)R12R13、-C(O)C2-C4烯基、-C(O)(CR9R10)CN、-C(O)OC1-C6烷基、-C(O)OC1-C6卤代烷基、-C(O)(CH2)nS(O)nC1-C6烷基、-C(O)C1-C3烷氧基C1-C6烷基、-C(O)NR5R6、-C(O)-(CH2)n-NR7C(O)R8、-CN、-(CH2)n-苯基、-C(O)-(CH2)n-苯基、-S(O)n-(CH2)n-苯基、-杂环基、-C(O)-(CH2)n-杂环基、-S(O)n-(CH2)n-杂环基,其中每个杂环基是5元或6元杂环基,所述杂环基可以是芳香族的、饱和的或部分饱和的并且可以含有从1至4个各自独立地选自由氧、氮和硫组成的组的杂原子,并且其中所述杂环基或苯基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基。
在本发明的一个实施例中,R4是C1-C2烷氧基-(例如甲氧基或乙氧基)。
在本发明的另一个实施例中,R4是-C(=O)C1-C3烷基(例如-C(C=O)甲基、-C(C=O)乙基、-C(C=O)i-丙基)。
在本发明的另一个实施例中,R4是-C(=O)C1-C3卤代烷基、更优选-C(=O)C1-C2氟烷基例如-C(=O)CH2F、-C(=O)CHF2、-C(=O)CF3)。
在本发明的一个实施例中,R4是-S(O)nC1-C6烷基、尤其是-S(O)2甲基或-S(O)2乙基。
在另一个实施例中,R4是-S(O)nC1-C6卤代烷基,例如-S(O)2氯甲基。
在另一个实施例中,R4是-S(O)n-(CH2)n-C3-C6环烷基,例如-S(O)2-(CH2)-c-丙基。
在本发明的另一个实施例中,R4是-C(O)OC1-C6烷基、尤其是-C(O)-O-甲基。
在本发明的另一个实施例中,R4是-S(O)nC(R11)R12R13或-C(O)C(R11)R12R13,其中R11是氢或甲基并且R12R13合起来是-CH2OCH2-(氧杂环丁烷-3-基)。
在本发明的另一个实施例中,R4是-C(O)-(CH2)n-C3-C6环烷基,例如-C(O)-c-丙基或-C(O)-(CH2)-c-丙基。
在本发明的另一个实施例中,R4是-C(O)(CR9R10)CN,例如-C(O)CH2CN、-C(O)CH(CH3)CN或-C(O)C(CH3)2CN。
在本发明的另一个实施例中,R4是-C(O)(CH2)nS(O)nC1-C6烷基,例如-C(O)CH2S(O)2甲基。
在本发明的另一个实施例中,R4是-C(O)C1-C3烷氧基C1-C6烷基,例如-C(O)CH2CH2-O-CH3或-C(O)CH(CH3)-O-CH3。
在本发明的另一个实施例中,R4是-C(O)NR5R6,尤其是其中R5是氢并且R6是C1-C6烷基,例如叔丁基。
在本发明的另一个实施例中,R4是-C(O)-(CH2)n-NR7C(O)R8,例如-C(O)-(CH2)-NR7C(O)R8或-C(O)NR7C(O)R8,例如-C(O)NHC(O)-叔丁基。
在本发明的另一个实施例中,R4选自由以下组成的组:-苯基、-C(O)-苯基、-S(O)n苯基,其中每个苯基如先前所定义的任选地被取代。
在本发明的另一个实施例中,R4是杂环基、-C(O)-杂环基或-S(O)n-杂环基。在另一个实施例中,每个前述杂环基是芳香族杂环基(即杂芳基),更优选地选自由以下组成的组:呋喃基、吡咯基、噻吩基、咪唑基、吡唑基、噁唑基、异噁唑基、噻唑基、吡喃基、吡啶基、吡嗪基、嘧啶基、哒嗪基和三唑基,更优选地选自由以下组成的组:吡啶基、哒嗪基、嘧啶基和吡嗪基,其中的每一个如先前所定义的任选地被取代。在另一个实施例中,每个前述杂环基是部分饱和的杂环基,更优选地选自由以下组成的组:咪唑啉基、异噁唑啉基和噻唑啉基,其中的每一个如先前所定义的任选地被取代。在另一个实施例中,每个前述杂环基是饱和的杂环基,更优选地选自由以下组成的组:吗啉基、四氢呋喃基和四氢吡喃基,其中的每一个如先前所定义的任选地被取代。
在本发明的一个实施例中,G选自由以下组成的组:氢、C1-C8烷基(例如甲基、乙基、正丙基、异丙基、正丁基、叔丁基、-C2-C8烯基(例如乙烯基)、C2-C8炔基(例如炔丙基)、-C(O)C1-C8烷基(更优选-C(O)C1-C6烷基,例如-C(O)异丙基和-C(O)叔丁基)和-C(O)-O-C1-C8烷基(更优选-C(O)-O-C1-C6烷基,例如-C(O)-O-甲基)。在优选的实施例中,G是氢。
取决于取代基的性质,具有式(I)的化合物可以以不同的异构体形式存在。当G是氢时,例如,具有式(I)的化合物可以以不同的互变异构体形式存在。
本发明覆盖所有此类异构体和互变异构体及其处于所有比例的混合物。此外,当取代基含有双键时,可能存在顺式和反式异构体。这些异构体也在所要求的具有式(I)的化合物的范围内。具有式(I)的化合物可以含有不对称中心并且可以作为单一对映异构体、以任何比例的对映异构体对而存在,或在存在多于一个不对称中心的情况下,含有所有可能比率的非对映异构体。典型地,与其他可能性相比,这些对映异构体之一具有增强的生物活性。
根据本发明的具有式(I)的化合物可以自身被用作除草剂,但是通常使用配制辅助剂(如载体、溶剂和表面活性剂(SFA))将它们配制成除草组合物。因此,本发明进一步提供了一种除草组合物,所述除草组合物包含根据前述权利要求中任一项所述的除草化合物和农业上可接受的配制辅助剂。尽管也可以制造即用型组合物,但是组合物可以是浓缩物的形式,所述浓缩物在使用之前被稀释。最终稀释通常用水进行,但是可以替代水或除了水之外用例如液体肥料、微量营养素、生物有机体、油或溶剂进行。
所述除草组合物总体上包含按重量计从0.1%至99%、尤其是按重量计从0.1%至95%的具有式(I)的化合物和按重量计从1%至99.9%的配制辅助剂,所述配制辅助剂优选地包含按重量计从0至25%的表面活性物质。
这些组合物可以选自多种配制品类型,这些配制品类型中的很多从Manual onDevelopment and Use of FAO Specifications for Plant Protection Products[关于植物保护产物的FAO标准的发展和使用的手册],第5版,1999年中已知。这些包括可尘化粉剂(DP)、可溶性粉剂(SP)、水溶性颗粒(SG)、水可分散性颗粒(WG)、可湿性粉剂(WP)、颗粒(GR)(缓释或快释的)、可溶性浓缩物(SL)、油易混合的液体(OL)、超低体积液体(UL)、可乳化性浓缩物(EC)、可分散性浓缩物(DC)、乳液(水包油(EW)和油包水(EO)两者)、微乳液(ME)、悬浮液浓缩物(SC)、气溶胶、胶囊悬浮液(CS)以及种子处理配制品。在任何情况下,所选择的配制品类型将取决于所设想的具体目的以及具有式(I)的化合物的物理、化学和生物特性。
可尘化粉剂(DP)可以通过将具有式(I)的化合物与一种或多种固体稀释剂(例如,天然粘土、高岭土、叶蜡石、膨润土、氧化铝、蒙脱石、砂藻土(kieselguhr)、白垩土、硅藻土(diatomaceous earth)、磷酸钙、碳酸钙和碳酸镁、硫、石灰、面粉、滑石和其他有机和无机的固体载体)混合并将所述混合物机械地碾磨成精细粉末来制备。
可溶性粉剂(SP)可以通过将具有式(I)的化合物与一种或多种水溶性无机盐(如碳酸氢钠、碳酸钠或硫酸镁)或一种或多种水溶性有机固体(如多糖)以及任选的一种或多种湿润剂、一种或多种分散剂或所述试剂的混合物进行混合以改进水分散性/水溶性来制备。然后将所述混合物碾磨成精细粉末。也可以将类似的组合物颗粒化以形成水溶性颗粒(SG)。
可湿性粉剂(WP)可以通过将具有式(I)的化合物与一种或多种固体稀释剂或载体、一种或多种湿润剂以及优选地一种或多种分散剂以及任选地一种或多种悬浮剂混合以促进在液体中的分散来制备。然后将所述混合物碾磨成精细粉末。也可以将类似的组合物颗粒化以形成水可分散性颗粒(WG)。
可以这样形成颗粒(GR):通过将具有式(I)的化合物与一种或多种粉状固体稀释剂或载体的混合物颗粒化来形成,或者通过将具有式(I)的化合物(或其在适宜试剂中的溶液)吸收进多孔颗粒材料(如浮石、凹凸棒石粘土、漂白土、砂藻土(kieselguhr)、硅藻土(diatomaceous earths)或玉米芯粉),或通过将具有式(I)的化合物(或其在适宜试剂中的溶液)吸附到硬芯材料(如沙、硅酸盐、矿物碳酸盐、硫酸盐或磷酸盐)上并且如果必要的话进行干燥来由预成型的空白颗粒形成。通常用于帮助吸收或吸附的试剂包括溶剂(如脂肪族和芳香族石油溶剂、醇、醚、酮以及酯)和粘着剂(如聚乙酸乙烯酯、聚乙烯醇、糊精、糖以及植物油)。也可以在颗粒中包含一种或多种其他添加剂(例如乳化剂、湿润剂或分散剂)。
可分散性浓缩物(DC)可以通过将具有式(I)的化合物溶于水或有机溶剂(如酮、醇或乙二醇醚)中来制备。这些溶液可以含有表面活性剂(例如以改进水稀释或防止喷雾罐中的结晶)。
可乳化性浓缩物(EC)或水包油乳液(EW)可以通过将具有式(I)的化合物溶于有机溶剂(任选地含有一种或多种湿润剂、一种或多种乳化剂或者所述试剂的混合物)中来制备。在EC中使用的合适的有机溶剂包括芳香族烃(如烷基苯或烷基萘,例如SOLVESSO 100、SOLVESSO 150和SOLVESSO 200;SOLVESSO是注册商标)、酮类(如环己酮或甲基环己酮)和醇类(如苯甲醇、糠醇或丁醇)、N-烷基吡咯烷酮类(如N-甲基吡咯烷酮或N-辛基吡咯烷酮)、脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲基酰胺)和氯化烃。EC产品可以在添加到水中时自发地乳化,从而产生具有足够稳定性的乳液,以允许通过适当设备进行喷雾施用。
EW的制备涉及获得呈液体(如果它在室温下不是液体,则它可以在典型地低于70℃的合理温度下熔化)或处于溶液中(通过将它溶于适当的溶剂中)的具有式(I)的化合物,并且然后在高剪切下将所得液体或溶液乳化进含有一种或多种SFA的水中,以产生乳液。在EW中使用的合适的溶剂包括植物油、氯化烃(如氯苯)、芳香族溶剂(如烷基苯或烷基萘)以及其他在水中具有低溶解度的适当的有机溶剂。
微乳液(ME)可以通过将水与一种或多种溶剂和一种或多种SFA的共混物混合,以自发地产生热力学稳定的各向同性的液体配制品来制备。具有式(I)的化合物最初存在于水中或溶剂/SFA共混物中。在ME中使用的合适的溶剂包括前文描述的在EC或EW中使用的那些。ME可以是水包油体系或油包水体系(存在哪种体系可以通过电导率测量来确定)并且可以适用于在同一配制品中将水溶性的和油溶性的杀有害生物剂混合。ME适合于稀释到水中,保持为微乳液或者形成常规的水包油乳液。
悬浮浓缩物(SC)可以包括具有式(I)的化合物的精细分散的不溶固体颗粒的水性或非水性悬浮液。SC可以通过在合适的介质(任选地具有一种或多种分散剂)中球磨或珠磨具有式(I)的固体化合物,以产生所述化合物的精细颗粒悬浮液来制备。在所述组合物中可以包括一种或多种湿润剂,并且可以包括悬浮剂以降低颗粒的沉降速率。可替代地,可以将具有式(I)的化合物干磨并且添加到含有前文描述的试剂的水中,以产生希望的终产物。
气溶胶配制品包含具有式(I)的化合物和合适的推进剂(例如,正丁烷)。也可以将具有式(I)的化合物溶于或分散于合适的介质(例如水或可与水混溶的液体,如正丙醇)中以提供在不加压的手动喷雾泵中使用的组合物。
胶囊悬浮液(CS)可以通过以与制备EW配制品类似的方式来制备,但具有另外的聚合阶段,使得获得油滴的水性分散体,其中每个油滴都被聚合物壳包封并且含有具有式(I)的化合物以及任选地,其载体或稀释剂。所述聚合物壳可以通过界面缩聚反应或通过凝聚程序来生产。这些组合物可以提供具有式(I)的化合物的受控释放并且它们可以用于种子处理。具有式(I)的化合物也可以被配制在可生物降解的聚合物基质中,以提供所述化合物的缓慢的受控释放。
组合物可以包含一种或多种添加剂以改进组合物的生物性能,例如通过改进在表面上的湿润性、保持力或分布;经处理的表面上的防雨性;或具有式(I)的化合物的吸收或流动。此类添加剂包括表面活性剂(SFA)、基于油的喷雾添加剂,例如某些矿物油或天然植物油(如大豆和油菜籽油),以及这些与其他生物增强辅助剂(可以帮助或改变具有式(I)的化合物的作用的成分)的共混物。
湿润剂、分散剂和乳化剂可以是阳离子类型、阴离子类型、两性类型或非离子类型的SFA。
合适的阳离子类型的SFA包括季铵化合物(例如鲸蜡三甲基溴化铵)、咪唑啉以及胺盐。
合适的阴离子SFA包括脂肪酸的碱金属盐、脂肪族硫酸单酯的盐(例如月桂硫酸钠)、磺化的芳香族化合物的盐(例如十二烷基苯磺酸钠、十二烷基苯磺酸钙、丁基萘磺酸盐以及二-异丙基-萘磺酸钠和三-异丙基-萘磺酸钠的混合物)、醚硫酸盐、醇醚硫酸盐(例如月桂醇聚醚-3-硫酸钠)、醚羧酸盐(例如月桂醇聚醚-3-羧酸钠)、磷酸酯(来自一种或多种脂肪醇与磷酸(主要是单酯)或与五氧化二磷(主要是二酯)之间反应的产物,例如月桂醇与四磷酸之间的反应;另外这些产物可以被乙氧基化)、硫代琥珀酰胺酸盐、石蜡或烯烃磺酸盐、牛磺酸盐以及木质磺酸盐。
合适的两性类型的SFA包括甜菜碱、丙酸盐和甘氨酸盐。
合适的非离子类型的SFA包括环氧烷(如环氧乙烷、环氧丙烷、环氧丁烷或其混合物)与脂肪醇(如油醇或鲸蜡醇)或与烷基酚(如辛基酚、壬基酚或辛基甲酚)的缩合产物;衍生自长链脂肪酸或己糖醇酐的偏酯;所述偏酯与环氧乙烷的缩合产物;嵌段聚合物(包含环氧乙烷和环氧丙烷);烷醇酰胺;单酯(例如脂肪酸聚乙二醇酯);氧化胺(例如月桂基二甲基氧化胺);和卵磷脂。
合适的悬浮剂包括亲水性胶体(如多糖、聚乙烯吡咯烷酮或羧甲基纤维素钠)和膨胀性粘土(如膨润土或凹凸棒石)。
本发明的组合物可以进一步包含至少一种另外的杀有害生物剂。例如,根据本发明的这些化合物也可以与其他除草剂或植物生长调节剂组合使用。在优选的实施例中,所述另外的杀有害生物剂是除草剂和/或除草剂安全剂。此类混合物的实例是(其中‘I’表示具有式(I)的化合物)。I+乙草胺、I+三氟羧草醚、I+三氟羧草醚-钠、I+苯草醚、I+丙烯醛、I+拉草、I+禾草灭、I+莠灭净、I+氨唑草酮、I+酰嘧磺隆、I+氯氨吡啶酸、I+杀草强、I+莎稗磷、I+磺草灵、I+莠去津、I+唑啶草酮、I+四唑嘧磺隆、I+BCPC、I+氟丁酰草胺、I+草除灵、I+苯酸草酮(bencarbazone)、I+氟草胺、I+呋草黄、I+苄嘧磺隆、I+苄嘧磺隆-甲基、I+地散磷、I+灭草松、I+双苯嘧草酮、I+双环磺草酮、I+吡草酮、I+二环吡喃酮(bicyclopyrone)、I+甲羧除草醚、I+双丙氨膦、I+双草醚、I+双草醚-钠、I+硼砂、I+除草定、I+溴丁酰草胺、I+溴苯腈、I+丁草胺、I+抑草磷、I+仲丁灵、I+丁苯草酮、I+丁草敌、I+二甲基胂酸、I+氯酸钙、I+唑草胺、I+卡草胺、I+唑草酮(carfentrazone)、I+唑酮草酯-乙基、I+整形醇、I+整形醇-甲基、I+氯草敏、I+氯嘧磺隆(chlorimuron)、I+氯嘧磺隆-乙基、I+氯醋酸、I+绿麦隆、I+氯苯胺灵、I+氯磺隆、I+敌草索(chlorthal)、I+敌草索-二甲基、I+吲哚酮草酯(cinidon-ethyl)、I+环庚草醚、I+醚磺隆、I+咯草隆、I+烯草酮、I+炔草酯(clodinafop)、I+炔草酯-炔丙基(clodinafop-propargyl)、I+广灭灵、I+氯甲酰草胺、I+克草立特、I+氯酯磺草胺(cloransulam)、I+氯酯磺草胺-甲基(cloransulam-methyl)、I+氰草津(cyanazine)、I+草灭特、I+cyclopyranile、I+环丙嘧磺隆(cyclosulfamuron)、I+草噻喃、I+氰氟草酯(cyhalofop)、I+氰氟草酯-丁基(cyhalofop-butyl)、I+2,4-D、I+杀草隆、I+茅草枯、I+棉隆(dazomet)、I+2,4-DB、I+I+甜菜安、I+麦草畏、I+敌草腈、I+滴丙酸、I+滴丙酸-P、I+禾草灵、I+禾草灵-甲基、I+双氯磺草安、I+野燕枯、I+野燕枯甲硫酸盐、I+吡氟草胺、I+氟吡草腙、I+噁唑隆、I+哌草丹、I+二甲草胺、I+异戊乙净、I+二甲吩草胺、I+二甲吩草胺-P、I+噻节因、I+二甲基次胂酸、I+氨氟灵、I+特乐酚、I+草乃敌、I+异丙净(dipropetryn)、I+敌草快、I+敌草快二溴化物、I+氟硫草定、I+敌草隆、I+茵多酸、I+EPTC、I+戊草丹、I+乙丁烯氟灵、I+胺苯磺隆、I+胺苯磺隆-甲基、I+乙烯利、I+乙氧呋草黄、I+氯氟草醚、I+乙氧嘧磺隆、I+乙氧苯草胺、I+精噁唑禾草灵(fenoxaprop-P)、I+精噁唑禾草灵-乙基(fenoxaprop-P-ethyl)、I+fenquinotrione、I+四唑酰草胺、I+硫酸亚铁、I+麦草伏-M、I+啶嘧磺隆、I+氯氟吡啶酯、I+双氟磺草胺、I+吡氟禾草灵(fluazifop)、I+吡氟禾草灵-丁基、I+吡氟禾草灵-P、I+精吡氟禾草灵(fluazifop-P-butyl)、I+异丙吡草酯(fluazolate)、I+氟酮磺隆、I+氟酮磺隆-钠、I+氟吡磺隆、I+氟消草、I+氟噻草胺、I+氟哒嗪(flufenpyr)、I+氟哒嗪-乙基、I+氟节胺(flumetralin)、I+唑嘧磺草胺、I+氟烯草酸(flumiclorac)、I+氟烯草酸-戊基、I+灭炔氟草胺、I+炔草胺(flumipropin)、I+伏草隆、I+乙羧氟草醚(fluoroglycofen)、I+乙羧氟草醚-乙基(fluoroglycofen-ethyl)、I+氟普(fluoxaprop)、I+氟胺草唑(flupoxam)、I+丙嘧草酯(flupropacil)、I+氟丙酸(flupropanate)、I+氟啶嘧磺隆、I+氟啶嘧磺隆-甲基-钠、I+抑草丁、I+氟啶草酮(fluridone)、I+氟咯草酮、I+氟草烟、I+呋草酮、I+嗪草酸、I+嗪草酸-甲基、I+氟磺胺草醚、I+甲酰胺磺隆、I+调节膦、I+草丁膦、I+草铵膦、I+草甘膦、I+哈劳克西芬、I+氯吡嘧磺隆、I+氯吡嘧磺隆-甲基、I+吡氟氯禾灵、I+吡氟氯禾灵-P、I+环嗪酮、I+咪草酸、I+咪草酸-甲基、I+甲氧咪草烟、I+甲基咪草烟、I+灭草烟、I+灭草喹、I+咪草烟、I+唑吡嘧磺隆、I+茚草酮、I+三嗪茚草胺(indaziflam)、I+碘甲烷、I+碘甲磺隆、I+碘甲磺隆-甲基-钠、I+碘苯腈、I+异丙隆、I+异噁隆、I+异噁草胺、I+异噁氯草酮、I+异噁唑草酮、I+异噁草醚(isoxapyrifop)、I+特胺灵、I+乳氟禾草灵、I+环草定、I+利谷隆、I+氯苯氧丙酸(mecoprop)、I+氯苯氧丙酸-P、I+苯噻草胺、I+氟磺酰草胺、I+二磺隆(mesosulfuron)、I+二磺隆-甲基、I+硝草酮、I+威百亩、I+噁唑酰草胺、I+苯嗪草酮、I+吡唑草胺、I+甲苯噻隆、I+灭草唑(methazole)、I+甲基胂酸、I+甲基杀草隆、I+异硫氰酸甲酯、I+异丙甲草胺、I+精异丙甲草胺、I+磺草唑胺、I+甲氧隆、I+嗪草酮、I+甲磺隆(metsulfuron)、I+甲磺隆-甲基(metsulfuron-methyl)、I+禾草特、I+绿谷隆、I+萘丙胺、I+敌草胺、I+敌草胺-M、I+萘草胺、I+草不隆、I+烟嘧磺隆、I+n-甲基草甘膦、I+壬酸、I+氟草敏、I+油酸(脂肪酸类)、I+坪草丹、I+嘧苯胺磺隆、I+氨磺乐灵、I+丙炔噁草酮、I+噁草酮、I+环氧嘧磺隆、I+氯噁嗪草、I+乙氧氟草醚、I+百草枯、I+百草枯二盐酸盐、I+克草敌、I+二甲戊乐灵、I+五氟磺草胺、I+五氯苯酚、I+甲氯酰草胺、I+环戊噁草酮、I+烯草胺、I+甜菜宁、I+毒莠定、I+氟吡酰草胺、I+唑啉草酯、I+哌草磷、I+丙草胺、I+氟嘧磺隆、I+氟嘧磺隆-甲基、I+氨氟乐灵、I+环苯草酮、I+调环酸钙(prohexadione-calcium)、I+扑灭通、I+扑草净、I+毒草胺、I+敌稗、I+喔草酯、I+扑灭津、I+苯胺灵、I+异丙草胺、I+丙苯磺隆、I+丙苯磺隆-钠、I+炔苯酰草胺、I+苄草丹、I+氟磺隆、I+双唑草腈、I+吡草醚、I+吡草醚-乙基、I+磺酰草吡唑(pyrasulfotole)、I+吡唑特、I+吡嘧磺隆、I+吡嘧磺隆-乙基、I+苄草唑、I+嘧啶肟草醚、I+稗草丹、I+氯苯咕醇(pyridafol)、I+哒草特、I+环酯草醚、I+嘧草醚、I+嘧草醚-甲基、I+吡丙醚(pyrimisulfan)、I+嘧草硫醚、I+嘧硫草醚-钠、I+吡咯磺隆(pyroxasulfone)、I+啶磺草胺(pyroxsulam)、I+二氯喹啉酸、I+氯甲喹啉酸、I+灭藻醌、I+喹禾灵(quizalofop)、I+精喹禾灵、I+玉嘧磺隆、I+苯嘧磺草胺、I+稀禾定、I+环草隆、I+西玛津、I+西草净、I+氯化钠、I+磺草酮、I+甲磺草胺、I+嘧磺隆、I+嘧磺隆-甲基、I+草硫膦、I+磺酰磺隆、I+硫酸、I+丁噻隆、I+呋喃磺草酮、I+环磺酮(tembotrione)、I+得杀草、I+特草定、I+特丁通、I+特丁津、I+去草净、I+甲氧噻草胺、I+噻草啶、I+噻吩磺隆、I+二噻酮磺隆(thiencarbazone)、I+噻吩磺隆-甲基、I+杀草丹、I+tolpyralate、I+苯吡唑草酮、I+三甲苯草酮、I+野麦畏、I+醚苯磺隆、I+三嗪氟草胺、I+苯磺隆(tribenuron)、I+苯磺隆-甲基、I+绿草定、I+草达津、I+三氟啶磺隆、I+三氟啶磺隆-钠、I+三氟草嗪(trifludimoxazin)、I+氟乐灵、I+氟胺磺隆、I+氟胺磺隆-甲基、I+三羟基三嗪、I+抗倒酯(trinexapac-ethyl)、I+三氟甲磺隆、I+[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-吡啶基氧基]乙酸乙酯(CAS RN353292-31-6)。本发明的化合物还可以与WO 06/024820和/或WO 07/096576中披露的除草化合物组合。
具有式(I)的化合物的混合配伍物还可以呈酯或盐的形式,如例如在ThePesticide Manual[杀有害生物剂手册],第十六版,英国作物保护委员会(British CropProtection Council),2012中所提到的。
具有式(I)的化合物还可以与具有其他农用化学品(如杀真菌剂、杀线虫剂或杀昆虫剂)以混合物使用,这些农用化学品的实例在The Pesticide Manual[杀有害生物剂手册]中给出。
具有式(I)的化合物与混合配伍物的混合比优选地是从1:100至1000:1。
这些混合物可以有利地用于以上提到的配制品中(在这种情况下“活性成分”涉及具有式(I)的化合物与混合配伍物的对应混合物)。
根据本发明的具有式(I)的化合物还可以与一种或多种安全剂组合使用。同样,根据本发明的具有式(I)的化合物与一种或多种另外的除草剂的混合物也可以与一种或多种安全剂组合使用。这些安全剂可以是AD 67(MON 4660)、解草嗪、解草喹、环丙磺酰胺(CASRN 221667-31-8)、二氯丙烯胺、解草唑-乙基、解草啶、氟草肟、解草噁唑和对应的R异构体、双苯噁唑酸-乙基、吡唑解草酸二乙酯、解草腈、N-异丙基-4-(2-甲氧基-苯甲酰基氨磺酰基)-苯甲酰胺(CAS RN221668-34-4)。其他可能性包括例如在EP 0365484中披露的安全剂化合物,例如N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。特别优选的是具有式(I)的化合物与环丙磺酰胺、双苯噁唑酸-乙基、解草喹和/或N-(2-甲氧基苯甲酰基)-4-[(甲基-氨基羰基)氨基]苯磺酰胺的混合物。
具有式(I)的化合物的安全剂还可以呈酯或盐的形式,如例如在The PesticideManual[杀有害生物剂手册],第16版(BCPC),2012中所提到的。对解草喹的提及还适用于其锂、钠、钾、钙、镁、铝、铁、铵、季铵、锍或鏻盐(如在WO 02/34048中披露的),并且对解草唑-乙基的提及还适用于解草唑等。
优选地,具有式(I)的化合物与安全剂的混合比是从100:1至1:10,尤其是从20:1至1:1。
所述混合物可以有利地用于以上提及的配制品中(在这种情况下“活性成分”涉及具有式(I)的化合物与安全剂的对应混合物)。
本发明仍进一步提供了一种在包括作物植物和杂草的场所处控制杂草的方法,其中所述方法包括向所述场所施用控制杂草量的根据本发明的组合物。‘控制’意指杀死、减少或延迟生长、或者防止或减少发芽。通常有待控制的植物是不想要的植物(杂草)。‘场所’意指植物正生长或将生长的区域。
具有式(I)的化合物的施用率可以在宽范围之内变化并且取决于土壤的性质、施用方法(出苗前或出苗后;拌种;施用至种子垄沟;免耕施用等)、作物植物、一种或多种有待控制的杂草、主要气候条件、以及受施用方法、施用时间以及目标作物支配的其他因素。根据本发明的具有式(I)的化合物通常以从10g/ha至2000g/ha、尤其是从50g/ha至1000g/ha的比率施用。
通常通过喷雾所述组合物进行施用,典型地是通过用于大面积的装在拖拉机上的喷雾机,但是还可以使用其他方法如撒粉(针对粉末)、滴加或者浸湿。
可以使用根据本发明的组合物的有用植物包括作物如谷物,例如大麦和小麦、棉花、油菜籽油菜、向日葵、玉米、稻、大豆、甜菜、甘蔗以及草皮。
作物植物还可以包括树,如果树、棕榈树、椰子树或其他坚果。还包括藤本植物(如葡萄)、灌木果树、果实植物和蔬菜。
作物应被理解为还包括通过常规的育种方法或通过基因工程已经赋予对除草剂或多种类别的除草剂(例如ALS-抑制剂、GS-抑制剂、EPSPS-抑制剂、PPO-抑制剂、ACC酶-抑制剂以及HPPD-抑制剂)的耐受性的那些作物。通过常规育种方法已经赋予其对咪唑啉酮(例如,甲氧咪草烟)的耐受性的作物的实例是夏季油菜(卡诺拉(canola))。通过基因工程方法已经赋予其对除草剂的耐受性的作物的实例包括例如草甘膦和草铵膦抗性玉米品种,这些玉米品种在和商标名下是可商购的。
作物还应被理解为通过基因工程方法已经赋予对有害昆虫的抗性的那些作物,例如Bt玉米(对欧洲玉米螟(European corn borer)有抗性)、Bt棉花(对棉铃象鼻虫(cottonboll weevil)有抗性)以及还有Bt马铃薯(对科罗拉多甲虫(Colorado beetle)有抗性)。Bt玉米的实例是的Bt 176玉米杂交体(先正达种子公司(Syngenta Seeds))。Bt毒素是由苏芸金芽孢杆菌土壤细菌天然形成的蛋白质。毒素或能够合成此类毒素的转基因植物的实例被描述在EP-A-451878、EP-A-374 753、WO 93/07278、WO 95/34656、WO 03/052073和EP-A-427 529中。包含一个或多个编码杀昆虫剂抗性并表达一种或多种毒素的基因的转基因植物的实例是(玉米)、Yield(玉米)、(棉花)、(棉花)、(马铃薯)、以及植物作物或其种子材料均可以是抗除草剂的并且同时是抗昆虫摄食的(“叠加的”转基因结果)。例如,种子可以在具有表达杀昆虫的Cry3蛋白的能力的同时是耐草甘膦的。
作物还应被理解为包括通过常规育种方法或基因工程获得并且含有所谓输出性状(例如改进的储存稳定性、更高的营养价值以及改进的香味)的那些作物。
其他有用的植物包括例如在高尔夫球场、草地、公园以及路旁的或者商业上种植用于草地的草皮草,以及观赏植物,如花卉或者灌木。
可以使用这些组合物来控制不想要的植物(统称为‘杂草’)。有待控制的杂草既可以是单子叶的物种,例如剪股颖属、看麦娘属、燕麦属、臂形草属、雀麦属、蒺藜草属、莎草属、马唐属、稗属、穇属、黑麦草属、雨久花属、筒轴茅属、慈姑属、藨草属、狗尾草属以及高粱属,也可以是双子叶的物种,例如苘麻属、苋属、豚草属、藜属、菊属、白酒草属、拉拉藤属、番薯属、旱金莲属、黄花稔属、白芥属、茄属、繁缕属、婆婆纳属、堇菜属以及苍耳属。本发明的化合物已经示出以展现出对抗某些禾本科植物杂草物种(尤其是多年生黑麦草(LoliumPerenne))的特别良好的活性。杂草还可以包括可被认为是作物植物但是在作物区外生长的植物(‘逃逸者(escapes)’),或从先前栽培的不同作物留下的种子生长的植物(‘志愿者(volunteers)’)。此类志愿者或逃逸者可以是对某些其他除草剂耐受的。
本发明的化合物可以根据以下方案来制备。
具有式(I)的化合物(其中G不为氢)可以通过使用已知的方法用试剂G-Z(其中G-Z是烷基化剂(如烷基卤)、酰化剂(如酰氯或酸酐)、磺酰化剂(如磺酰氯)、氨基甲酰化剂(如氨基甲酰氯)或者碳酸化剂(如氯甲酸盐))处理具有式(I)的化合物(其中G是氢))来制备。
具有式(I)的化合物可以通过在合适的钯催化剂、碱的存在下并且在合适的溶剂中,使具有式(A)的碘叶立德(iodonium ylide)(其中Ar是任选取代的苯基)与具有式(B)的芳基硼酸反应来制备。
合适的钯催化剂总体上是钯(II)或钯(0)络合物,例如二卤化钯(II)、乙酸钯(II)、硫酸钯(II)、双(三苯基膦)-二氯化钯(II)、双(三环戊基膦)二氯化钯(II)、双(三环己基-膦)二氯化钯(II)、双(二苯亚甲基丙酮)钯(0)或四-(三苯基膦)钯(0)。所述钯催化剂还可以由钯(II)或钯(0)化合物通过与所希望的配体络合(通过例如使有待络合的钯(II)盐(例如二氯化钯(II)(PdCl2)或乙酸钯(II)(Pd(OAc)2))与所希望的配体(例如三苯基膦(PPh3)、三环戊基膦、三环已基膦、2-二环己基膦基-2',6'-二甲氧基联苯基或2-二环己基膦基-2',4',6'-三异丙基联苯基)以及选择的溶剂一起与具有式(N)的化合物、具有式(O)的芳基硼酸、以及碱组合)来“原位”制备。还合适的是二齿配体,例如1,1'-双(二苯基膦基)二茂铁或1,2-双(二苯基膦基)乙烷。通过加热反应介质,C-C偶联反应所需的钯(II)络合物或钯(0)络合物因此“原位”形成,并且然后引发C-C偶联反应。
钯催化剂是基于具有式(N)的化合物以从0.001mol%至50mol%的量、优选以从0.1mol%至15mol%的量使用。反应还可以在其他添加剂(如四烷基铵盐,例如四丁基溴化铵)存在下进行。优选地,钯催化剂是乙酸钯,碱是氢氧化锂并且溶剂是水性1,2-二甲氧基乙烷。
具有式(A)的化合物可以使用已知程序,在溶剂(如水或醇的水溶液,如乙醇的水溶液)中,用高价碘试剂(如(二乙酰氧基)碘苯或亚碘酰苯)以及碱(如水性碳酸钠、氢氧化锂或氢氧化钠)进行处理来从具有式(C)的1,3二酮化合物制备。
可替代地,R1基团可稍后在合成序列中通过铃木(Suzuki)或施蒂勒(Stille)偶联分别加成到适当的硼酸或锡烷,如在以下方案4a的步骤2中。或者,类型E2的中间体的铱催化的硼基化可以提供硼酸酯,所述硼酸酯经铃木偶联可以提供类型I的化合物(方案4b)。或者化合物E中的卤素可以转化为硼酸酯,并且然后铃木偶联可以提供产物(方案4c)。
可替代地,铜催化的吡唑与类型E的中间体偶联可以提供其中R1为适当取代的吡唑的化合物。
硼酸可以通过如以下方案5中的方法制备。例如,具有式(B)或(D)的化合物可以通过已知方法从具有式(F)或(H)的芳基卤制备。例如,可以在合适的溶剂(优选二乙醚或四氢呋喃)中,在-80℃与30℃之间的温度下,用烷基锂卤化物或烷基镁卤化物处理具有式(F)或(H)的芳基卤,并且然后可以使获得的芳基镁或芳基锂试剂与硼酸三烷基酯(优选硼酸三甲酯)反应以得到硼酸芳基二烷基酯,可以使所述硼酸芳基二烷基酯在酸性条件下进行水解以提供具有式(B)或(D)的硼酸。
如以下方案中示出,具有式(I)的化合物也可以通过Pb偶联,通过使具有式(D)的化合物反应以形成具有式(J)的有机铅试剂并且随后与1,3二酮(C)在例如由J.Pinhey,Pure and Appl.Chem.[纯粹与应用化学],(1996),68(4),819和由M.Moloney等人,Tetrahedron Lett.[四面体快报],(2002),43,3407描述的条件下反应来制备。合适的三芳基铋化合物在例如由A.Yu.Fedorov等人,Russ.Chem.Bull.Int.Ed.[俄罗斯化学公报国际版],(2005),54(11),2602,以及由P.Koech和M.Krische,J.Am.Chem.Soc.[美国化学会志],(2004),126(17),5350以及其中的参考文献描述的条件下可用作相关程序。
如以下方案中示出,类型(I)的化合物也可以通过钯偶联制备,其中类型(B)的硼酸以铃木(Suzuki)类型偶联来偶联至适当保护的类型(K)的卤代烯烃。
在合适的条件下,合适的1,3二酮也可以在钯催化下直接偶联至卤代化合物(例如具有式(L))。如前所述的中间体(M)的芳基化得到类型(I)的化合物。可替代地,可以将类型L1的化合物偶联、硼基化(如前所述)、并且再次偶联以得到所希望的产物(方案8b)。
具有式(I,G=H)的化合物可以通过与由T.Wheeler,US4,209,532描述的方法的类似方法,通过使具有式(N)的化合物(其中R是氢或烷基)优选地在酸或碱的存在下并且任选地在合适溶剂的存在下环化来制备。具有式(N)的化合物已经被特别设计为合成具有式(I)的化合物的中间体。具有式(N)的化合物(其中R是氢)可以在酸性条件下、优选地在强酸(如硫酸、多磷酸或伊顿试剂(Eaton's reagent))的存在下、任选地在合适溶剂(如乙酸、甲苯或二氯甲烷)的存在下被环化。
如以下方案中示出,类型(I)的化合物也可以使用合适的保护基团通过后期官能化制备。化合物(Q)可以通过所述方法转化为中间体(R),并且然后可以除去保护基团(如示出的BOC基团)(在此实例中在酸性条件下)。然后,中间体(S)可以直接转化为化合物(例如(U)),或者在氧原子和氮原子上双重反应,以得到类型(T)的化合物。类型(T)的化合物可以容易地转化为类型(I)的任何化合物-例如,(T)的烯醇酯可以选择性水解以得到(U,G=H),然后其可以通过前述方法转化为(U,G不是H)。
可替代地,所述序列可以用磺酰化而不是酰化进行,如本领域技术人员已知的。
脲、酰基脲、N-杂芳基和N-氰基化合物可以由中间体(S),也通过如本领域技术人员已知的标准文献方法制成,如在方案12中。
(a)2-异氰酸基-2-甲基-丙烷,NEt3,DCM;(b)异氰酸2,2-二甲基丙酰酯,NEt3,DCM;(c)2-氟嘧啶,NEt3,DMSO,180℃,微波;(d)溴化氰,DIPEA,DCM。
方案12
可以使用如以下示出的方法制备如这些的1,3二酮。所以可商购的酮(例如类型(V)的)可转化为中间体(Y),并且然后转化为中间体(Z),并且最后脱羧得到中间体(Q)(这些方法描述于WO 2008/110308中)。
以下非限制性实例为本发明的代表性化合物(如在下表1和2中所提及的)提供了特定的合成方法。
实例1:9-[4-(5-氟嘧啶-2-基)-2,6-二甲基-苯基]-3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮(化合物A2)的合成。
步骤1:1-(1-甲氧基-4-亚哌啶基)丙-2-酮的合成
在0℃-5℃下向KOH(30.4g,542mmol)在乙醇(440.0mL)和水(115.0mL)中的搅拌溶液中逐滴添加1-二甲氧基磷酰基丙-2-酮(75.0mL,542mmol)。然后分批添加1-甲氧基哌啶-4-酮(50.0g,387mmol),保持内部温度恒定。在室温下搅拌反应混合物过夜。在减压下蒸发大部分溶剂。将残余物用DCM和水稀释,并且水层用DCM萃取两次。将合并的有机物用盐水洗涤、经Na2SO4干燥、过滤并在减压下蒸发以获得粗残余物,将所述粗残余物通过快速柱色谱法以获得1-(1-甲氧基-4-亚哌啶基)丙-2-酮(60g)
1H NMR(CDCl3)δ6.02(s,1H),3.53(s,3H),3.44-3.16(m,3H),2.69-2.62(m,3H),2.36-2.35(m,2H),2.17(s,3H)。
步骤2:3-甲氧基-8,10-二氧代-3-氮杂螺[5.5]十一烷-11-甲酸乙酯的合成
在室温下向1-(1-甲氧基-4-亚哌啶基)丙-2-酮(20.0g,118mmol)在干燥乙醇(164.0mL)中的搅拌溶液中添加丙二酸二乙酯(18.0mL,118mmol),然后逐滴添加乙醇钠(21.0%,49.8g,275mL,154mmol)。将反应混合物在室温下搅拌3h,然后回流2h,然后使其在室温下过夜。然后在减压下蒸发掉溶剂,将粗品用水稀释并用乙酸乙酯洗涤。然后将水层用水性柠檬酸(10%)酸化、用固体NaCl饱和、并用乙酸乙酯萃取。将合并的有机物用盐水洗涤并且经Na2SO4干燥、过滤、浓缩以获得粗残余物,将所述粗残余物用正己烷磨碎、倾析并且将所获得的残余物干燥以获得棕色胶状物,将所述棕色胶状物以粗品形式带入下一步骤。
步骤3:3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮的合成
将3-甲氧基-8,10-二氧代-3-氮杂螺[5.5]十一烷-11-甲酸乙酯(27.8g,98.1mmol)吸收进乙醇(70.0mL)中。在室温下添加氢氧化钠(12.0M,140mL,1685mmol),并将反应混合物在室温下搅拌过周末。然后将反应混合物蒸发,并在0℃下用10%柠檬酸溶液酸化至pH 5-6,用饱和NaCl洗涤,用乙酸乙酯萃取几次。将合并的有机物用盐水洗涤并且经Na2SO4干燥、过滤、浓缩以得到棕色粘性固体。将其用正己烷磨碎,在倾析己烷后,将所得固体在减压下干燥以获得3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮浅棕色固体;(16g)。
1H NMR(DMSO-D6)δ11.06(bs,1H),5.17(s,1H),3.39(s,3H),3.05(bs,4H),2.31-2.13(m,4H),1.63(bs,2H),1.40(bs,2H)。
步骤4:9-(4-溴-2,6-二甲基-苯基)-3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮的合成
向在氮气下的3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮(7.36g,34.8mmol)在氯仿(200mL)中的搅拌溶液中添加4-二甲基氨基吡啶(21.3g,174mmol)。将反应混合物在室温下搅拌15分钟,然后添加甲苯(99.0mL),然后添加在氯仿(130mL)中的[二乙酰氧基-(4-溴-2,6-二甲基-苯基)铅烷基]乙酸酯(19.8g,34.8mmol)。将反应混合物在80℃下搅拌3h,并且然后使其在室温下静置过夜。将反应混合物用10%柠檬酸酸化,并将混合物通过硅藻土过滤。将所述硅藻土用氯仿洗涤,并且水层用氯仿萃取两次。将合并的有机物用盐水洗涤、经Na2SO4干燥、过滤并且蒸发以获得棕色胶状物。将其通过快速柱色谱法纯化以得到呈白色固体的9-(4-溴-2,6-二甲基-苯基)-3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮(7.5g)
1H NMR(DMSO-D6):δ10.53(bs,1H),7.18(s,2H),3.41(s,3H),3.11-3.02(m,2H),2.67(m,2H),2.33-2.28(m,4H),1.95(s,6H),1.79(bs,2H),1.50(bs,2H)。
步骤5:9-[2,6-二甲基-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯基]-3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮的合成
将9-(4-溴-2,6-二甲基-苯基)-8-羟基-3-甲氧基-3-氮杂螺[5.5]十一-8-烯-10-酮(1.00g,2.54mmol)与4,4,5,5-四甲基-2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-1,3,2-二氧杂环戊硼烷(1.93g,7.61mmol)、乙酸钾(0.747g,7.61mmol)、Pd2dba3(0.232g,0.254mmol)和S-Phos配体(0.208g,0.507mmol)在1,4-二噁烷(20mL)中组合。通过在氮气鼓泡下搅拌将混合物脱气15分钟,然后在120℃的油浴中加热4h。后处理和通过快速柱色谱法的纯化得到9-[2,6-二甲基-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯基]-3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮(LC-MS:M+H=442)。
步骤6:9-[4-(5-氟嘧啶-2-基)-2,6-二甲基-苯基]-3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮(化合物A2)的合成。
将9-[2,6-二甲基-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯基]-3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮(3.60g,6.48mmol)、2-溴-5-氟-嘧啶(1.15g,6.48mmol)、PdCl2(dppf).DCM(1.06g,1.30mmol)和K3PO4(5.50g,25.9mmol)吸收进1,2-二甲氧基乙烷(50.0mL)中。然后添加水(25.0mL)。将溶液用氮气脱气30分钟。将反应混合物在100℃下回流3h。将反应混合物过滤并蒸发以获得粗残余物,将所述粗残余物通过快速柱色谱法纯化并且随后磨碎和金属清除(二氧化硅负载的丙硫醇树脂)以得到呈白色固体的9-[4-(5-氟嘧啶-2-基)-2,6-二甲基-苯基]-3-甲氧基-3-氮杂螺[5.5]十一烷-8,10-二酮。
1H NMR(400MHz,甲醇-d4)δ=8.77-8.68(m,2H),8.07-8.00(m,2H),3.56-3.46(m,3H),3.25-3.11(m,2H),2.77-2.60(m,4H),2.57-2.39(m,2H),2.17-2.08(m,6H),2.04-1.92(m,2H),1.75-1.58(m,2H)。
实例2:3-乙酰基-9-[4-(5-氟嘧啶-2-基)-2,6-二甲基-苯基]-3-氮杂螺[5.5]十一烷-8,10-二酮(化合物A13)的合成。
步骤1:O3-叔丁基O11-乙基8,10-二氧代-3-氮杂螺[5.5]十一烷-3,11-二甲酸酯的合成
将4-亚丙酮基哌啶-1-甲酸叔丁酯(12.9g,54.0mmol)溶解在乙醇(100mL)中并添加丙二酸二乙酯(54.12mmol)。将反应混合物用乙醇钠的溶液处理,所述溶液是通过在室温下将钠(54.1mmol)添加到乙醇(30mL)中制备的。将反应混合物在室温下搅拌3小时,然后加热至回流持续1小时。冷却后,将反应混合物在真空中浓缩,以得到呈油状物的O3-叔丁基O11-乙基8,10-二氧代-3-氮杂螺[5.5]十一烷-3,11-二甲酸酯,将其不经进一步纯化而用于下一步骤。
步骤2:8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯的合成
将来自步骤1的粗O3-叔丁基O11-乙基8,10-二氧代-3-氮杂螺[5.5]十一烷-3,11-二甲酸酯溶解在水性NaOH(12M,5mL)中并搅拌5小时。通过在0℃下添加浓HCl将反应混合物酸化至pH 6并用EtOAc萃取。将有机物干燥并在真空中浓缩以留下黄色固体,将其磨碎产生8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯的淡粉色粉末。通过添加浓HCl将水层进一步酸化至pH 2并用EtOAc萃取。将有机物干燥并在真空中浓缩以留下淡黄色固体,将其用乙醚磨碎得到另一批8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯的淡黄色粉末(3.914g,13.91mmol)。1H NMR(400MHz,CDCl3)3.51-3.25(m,4H),2.69-2.54(m,4H),1.47-1.43(m,9H),1.44-1.39(m,4H)。
步骤3:9-(4-溴-2,6-二甲基-苯基)-8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯的合成
将8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯(0.5g,1.8mmol)和DMAP(1.1g,8.9mmol)溶解在氯仿(20mL)中。在氮气下将反应混合物搅拌10分钟并添加甲苯(5mL),然后添加[二乙酰氧基-(4-溴-2,6-二甲基-苯基)铅烷基]乙酸酯(1.2g,2.1mmol)。在氮气下在75℃下将所得悬浮液加热3小时,并且然后允许其冷却至室温。将反应混合物用2M HCl(50mL)处理并在搅拌下形成白色沉淀物。将混合物过滤并将有机相分离,并将水层用DCM萃取。将合并的有机物干燥(MgSO4),蒸发并通过快速柱色谱法(梯度洗脱:5%-100%EtOAc:异己烷)纯化,以得到9-(4-溴-2,6-二甲基-苯基)-8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯(0.51g,1.1mmol)。1H NMR(400MHz,甲醇-d4)7.25-7.10(m,2H),3.54-3.43(m,4H),2.61-2.52(m,4H),2.05-1.98(m,6H),1.72-1.56(m,4H),1.48-1.39(m,9H)。
步骤4:9-(4-溴-2,6-二甲基-苯基)-8-甲氧基-10-氧代-3-氮杂螺[5.5]十一-8-烯-3-甲酸叔丁酯的合成
将9-(4-溴-2,6-二甲基-苯基)-8,10-二氧代-3-氮杂螺[5.5]十一烷-3-甲酸叔丁酯(1.150g,2.476mmol)悬浮在丙酮(50mL)中,然后添加碳酸钾(1.500当量,3.714mmol),然后添加碘甲烷(5当量,12.38mmol)。在室温下搅拌反应混合物24小时。然后将反应混合物在真空中浓缩,然后通过小心地稀释到2M HCl(泡腾)中淬灭,并用EtOAc萃取两次。将有机物干燥并且在真空中浓缩以留下呈橙色泡沫的9-(4-溴-2,6-二甲基-苯基)-8-甲氧基-10-氧代-3-氮杂螺[5.5]十一-8-烯-3-甲酸叔丁酯(1.180g,2.467mmol,99%)。
1H NMR(500MHz,CDCl3)δ=7.20-7.13(m,2H),3.64-3.53(m,5H),3.38-3.28(m,2H),2.64-2.49(m,4H),2.05-2.01(m,6H),1.72-1.63(m,4H),1.48-1.43(m,9H)
步骤5:9-[2,6-二甲基-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯基]-8-甲氧基-10-氧代-3-氮杂螺[5.5]十一-8-烯-3-甲酸叔丁酯的合成
将9-(4-溴-2,6-二甲基-苯基)-8-甲氧基-10-氧代-3-氮杂螺[5.5]十一-8-烯-3-甲酸叔丁酯与4,4,5,5-四甲基-2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-1,3,2-二氧杂环戊硼烷(1.500当量,3.700mmol)、乙酸钾(1.500当量,3.700mmol)、(1E,4E)-1,5-二苯基戊-1,4-二烯-3-酮钯(0.04当量,0.09866mmol)和二环己基-[2-(2,6-二甲氧基苯基)苯基]磷烷(0.08当量,0.1973mmol)在1,4-二噁烷(21mL)中组合,并用2个真空/N2循环吹扫烧瓶。将混合物在100℃下加热过夜。然后添加4,4,5,5-四甲基-2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-1,3,2-二氧杂环戊硼烷(1.500当量,3.700mmol)、(1E,4E)-1,5-二苯基戊-1,4-二烯-3-酮钯(0.04当量,0.09866mmol)和二环己基-[2-(2,6-二甲氧基苯基)苯基]磷烷(0.08当量,0.1973mmol),并将反应混合物再加热6h。然后添加4,4,5,5-四甲基-2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-1,3,2-二氧杂环戊硼烷(1.500当量,3.700mmol)、(1E,4E)-1,5-二苯基戊-1,4-二烯-3-酮钯(0.04当量,0.09866mmol)和二环己基-[2-(2,6-二甲氧基苯基)苯基]磷烷(0.08当量,0.1973mmol),并将反应混合物加热过夜。然后添加4,4,5,5-四甲基-2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-1,3,2-二氧杂环戊硼烷(1.500当量,3.700mmol)、(1E,4E)-1,5-二苯基戊-1,4-二烯-3-酮钯(0.04当量,0.09866mmol)和二环己基-[2-(2,6-二甲氧基苯基)苯基]磷烷(0.08当量,0.1973mmol),并将反应混合物加热过周末。在冷却后,将反应混合物用2M HCl稀释并用EtOAc萃取两次。将有机物干燥并在真空中浓缩以留下橙色固体,将其通过快速柱色谱法(梯度洗脱:5%-60%EtOAc:异己烷)纯化以得到呈橙色胶状物的9-[2,6-二甲基-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯基]-8-甲氧基-10-氧代-3-氮杂螺[5.5]十一-8-烯-3-甲酸叔丁酯(0.133g,0.253mmol)。
1H NMR(400MHz,CDCl3)δ7.53-7.46(m,2H),3.62-3.56(m,2H),3.56-3.47(m,3H),3.42-3.28(m,2H),2.62-2.53(m,4H),2.10-2.05(m,6H),1.74-1.62(m,4H),1.49-1.44(m,9H),1.28-1.25(m,12H)
步骤6:9-[4-(5-氟嘧啶-2-基)-2,6-二甲基-苯基]-8-甲氧基-10-氧代-3-氮杂螺[5.5]十一-8-烯-3-甲酸叔丁酯的合成
将9-[2,6-二甲基-4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苯基]-8-甲氧基-10-氧代-3-氮杂螺[5.5]十一-8-烯-3-甲酸叔丁酯(0.460g,0.875mmol)和2-氯-5-氟-嘧啶(1.2当量,1.05mmol)吸收进微波小瓶中的1,2-二甲氧基乙烷(6.15mL/mmol)中。添加PdCl2(dppf).DCM(0.2当量,0.175mmol),然后添加溶于水(1.54mL/mmol,75mmol)的磷酸三钾(4.0当量,3.50mmol)的溶液。将混合物在微波中加热至100℃持续45分钟。在冷却后,将反应混合物用水稀释并用EtOAc萃取两次。将有机物分离,然后经硫酸镁干燥并在真空中浓缩以留下深棕色胶状物,将其通过快速柱色谱法纯化以得到9-[4-(5-氟嘧啶-2-基)-2,6-二甲基-苯基]-8-甲氧基-10-氧代-3-氮杂螺[5.5]十一-8-烯-3-甲酸叔丁酯(0.214g,0.432mmol)。
1H NMR(400MHz,CDCl3)δ8.68-8.52(m,2H),8.10-7.96(m,2H),3.68-3.53(m,5H),3.42-3.30(m,2H),2.68-2.49(m,4H),2.19-2.00(m,6H),1.76-1.60(m,4H),1.51-1.41(m,9H)
步骤7:3-乙酰基-9-[4-(5-氟嘧啶-2-基)-2,6-二甲基-苯基]-3-氮杂螺[5.5]十一烷-8,10-二酮(化合物A13)的合成。
将9-[4-(5-氟嘧啶-2-基)-2,6-二甲基-苯基]-8-甲氧基-10-氧代-3-氮杂螺[5.5]十一-8-烯-3-甲酸叔丁酯(0.187g,0.377mmol)在室温下在氯化氢(在1,4-二噁烷中4M,5mL,20mmol)中搅拌1小时,在所述时间后将反应混合物在真空中浓缩以留下淡黄色固体。将此材料悬浮在二氯甲烷(5mL)中。添加N,N-二乙基乙胺(2当量,0.754mmol),然后添加乙酰氯(2.5当量,0.942mmol),此时所有固体进入溶液中,并将反应混合物在室温下搅拌1.5小时。将反应混合物用2M HCl稀释并用DCM萃取两次。将有机物在真空中浓缩以留下黄色固体,将其吸收进丙酮(5.89mL/mmol)中。添加HCl(2M溶液)(5.89mL/mmol,4.44mmol),并将反应混合物在60℃下加热3小时,在此时间期间,灰白色固体从溶液中析出。冷却反应混合物、过滤并在烧结物(sinter)上干燥得到呈奶油色粉末的3-乙酰基-9-[4-(5-氟嘧啶-2-基)-2,6-二甲基-苯基]-3-氮杂螺[5.5]十一烷-8,10-二酮(0.1100g,0.2597mmol)。
1H NMR(400MHz,甲醇-d4)δ=8.78-8.68(m,2H),8.08-8.03(m,2H),3.68-3.55(m,4H),2.70-2.57(m,4H),2.17-2.14(m,6H),2.13-2.11(m,3H),1.83-1.64(m,4H)
本发明的除草化合物的实例。
表1
表2
表3.现有技术比较.
生物实例
将各种测试物种的种子播种在盆内的标准土壤中(多年生黑麦草(Loliumperenne)(LOLPE)、大狗尾草(Setaria faberi)(SETFA)、大穗看麦娘(Alopecurusmyosuroides)(ALOMY)、稗草(Echinochloa crus-galli)(ECHCG)、野燕麦(Avena fatua)(AVEFA))。在温室中在受控条件(在24℃/16℃,白天/夜晚;14小时光照;65%湿度)下培养一天后(出苗前)或8天培养后(出苗后),用水性喷雾溶液喷雾这些植物,所述水性喷雾溶液源自技术活性成分在丙酮/水(50:50)溶液中的配制品,所述溶液含有0.5%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。化合物以250g/h施用。然后使测试植物在温室中在受控条件下在温室(24℃/16℃,白天/夜晚;14小时光照;65%湿度)中生长,并且每日浇水两次。对于出苗前和出苗后13天后,对所述测试给植物造成的损害百分比进行评价。下表中以五分制示出了生物活性(5=80%-100%;4=60%-79%;3=40%-59%;2=20%-39%;1=0-19%)。
表B1
NT=未测试。
使用以上程序概述,将杂草物种ALOMY、AVEFA和LOLPE在出苗后用本发明的化合物A4或比较化合物C1(来自WO2008/110308的化合物T-26)以指示的施用量进行处理。对所述测试给植物造成的损害百分比进行评价。
表B2.
这些结果表明,与结构类似的现有技术化合物C1相比,本发明化合物(使用化合物A4、A7和A13例示)展现出改进的杂草控制。
Claims (15)
1.一种具有式(I)的化合物
其中
R1选自甲基、苯基和包含一个或两个氮杂原子的5元或6元杂芳基,所述苯基和杂芳基任选地被一个或两个R15取代基取代;
R2是甲基或甲氧基;
R3是甲基或甲氧基;
R4选自由以下组成的组:C1-C4烷基、C1-C4烷氧基-、C1-C4卤代烷基、-C(=O)C1-C4烷基、-C(=O)C1-C4卤代烷基、-S(O)nC1-C6烷基、-S(O)nC1-C6卤代烷基、-S(O)n-(CH2)n-C3-C6环烷基、-S(O)nC(R11)R12R13、-C(O)H、-C(O)-(CH2)n-C3-C6环烷基、-C(O)C(R11)R12R13、-C(O)C2-C4烯基、-C(O)(CR9R10)CN、-C(O)(CR9R10)(CR9R10)CN、-C(O)CH2C(O)-C1-C6烷基、-C(O)CH2OC(O)-C1-C6烷基、-C(O)OC1-C6烷基、-C(O)OC1-C6卤代烷基、-C(O)(CH2)nS(O)nC1-C6烷基、-C(O)C1-C3烷氧基C1-C6烷基、-C(O)C1-C3烷氧基C2-C6烯基、-C(O)C1-C3烷氧基C2-C6炔基、-C(O)C1-C3烷氧基C1-C6卤代烷基、-C(O)C1-C3烷氧基C3-C6环烷基、-C(O)OC1-C3烷氧基C1-C6烷基、-C(O)C1-C3烷氧基C1-C3烷氧基C1-C6烷基、-C(O)(CH2)nNR5R6、-C(O)-(CH2)n-NR7C(O)R8、-C(O)-(CH2)n-O-N=CR5R5、-CN、-(CH2)n-苯基、-C(O)-(CH2)n-苯基、-S(O)n-(CH2)n-苯基、-杂环基、-C(O)-(CH2)n-杂环基、-C(O)(CH2)nO-(CH2)n-杂环基、-S(O)n-(CH2)n-杂环基,其中每个杂环基是5元或6元杂环基,所述杂环基可以是芳香族的、饱和的或部分饱和的并且可以含有从1至4个各自独立地选自由氧、氮和硫组成的组的杂原子,并且其中所述杂环基或苯基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
R5选自由氢和C1-C6烷基组成的组;
R6选自由以下组成的组:氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6卤代烷基、羟基-、C1-C6烷氧基、C3-C6环烷基、-C1-C4烷氧基C1-C6烷基、-C1-C3烷氧基C1-C6卤代烷基、-(CR9R10)C1-C6卤代烷基、-(CR9R10)C(O)NR5R5、苯基、-吡啶基,其中所述苯基和吡啶基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;或者
R5和R6一起形成-CH2CH2OCH2CH2-;并且
R7选自由氢和C1-C6烷基组成的组;
R8选自由以下组成的组:氢、C1-C6烷基、C1-C6烷氧基、C3-C6环烷基、苯基、-吡啶基,其中所述苯基和吡啶基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
R9是氢或甲基;
R10是氢或甲基;或者
R9和R10一起形成-CH2CH2-;并且
R11是氢或甲基;
R12选自由以下组成的组:氢、C1-C6烷基、羟基和C1-C6烷氧基-;
R13选自由以下组成的组:氢、C1-C6烷基、羟基和C1-C6烷氧基;或者
R12和R13一起形成-CH2-X-CH2-;并且
X选自由O、S和N-R14组成的组;
R14选自由以下组成的组:氢、C1-C3烷基和C1-C3烷氧基-;
R15独立地选自由以下组成的组:C1-C4烷基、C1-C4卤代烷基、氰基和卤素;
G选自由以下组成的组:氢、-(CH2)n-Ra、-C(O)-Ra、-C(O)-(CRcRd)n-O-Rb、-C(O)-(CRcRd)n-S-Rb、-C(O)NRaRa、-S(O)2-Ra和C1-C8烷氧基-C1-C3烷基-;
Ra独立地选自由以下组成的组:氢、C1-C8烷基、C1-C3卤代烷基、C2-C8烯基、C2-C8炔基、C3-C6环烷基、杂环基和苯基,其中所述杂环基和苯基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
Rb选自由以下组成的组:C1-C8烷基、C1-C3卤代烷基、C2-C8烯基、C2-C8炔基、C3-C6环烷基、杂环基和苯基,其中所述杂环基和苯基任选地被一个、两个或三个独立地选自由以下组成的组的取代基取代:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C2-C3烯基、C2-C3炔基、卤素、氰基和硝基;
Rc是氢或C1-C3烷基;
Rd是氢或C1-C3烷基;并且
n独立地是0、1或2;
或其农业上可接受的盐。
2.根据权利要求1所述的化合物,其中,R2是甲基。
3.根据前述权利要求中任一项所述的化合物,其中,R3是甲基。
4.根据前述权利要求1至2中任一项所述的化合物,其中,R3是甲氧基。
5.根据前述权利要求中任一项所述的化合物,其中,R4是C1-C4烷氧基-。
6.根据权利要求1至4中任一项所述的化合物,其中,R4是-C(=O)C1-C4烷基。
7.根据权利要求1至4中任一项所述的化合物,其中,R4是-C(O)OC1-C6烷基。
8.根据前述权利要求中任一项所述的化合物,其中,G是氢。
9.根据权利要求1至7中任一项所述的化合物,其中,G是-C(O)C1-C6烷基。
10.根据权利要求1至7中任一项所述的化合物,其中,G是-C(O)-O-C1-C6烷基。
11.一种除草组合物,其包含根据前述权利要求中任一项所述的具有式(I)的化合物、和农业上可接受的配制辅助剂。
12.根据权利要求11所述的除草组合物,其进一步包含至少一种另外的杀有害生物剂。
13.根据权利要求12所述的除草组合物,其中,所述另外的杀有害生物剂是除草剂或除草剂安全剂。
14.一种在场所控制杂草的方法,所述方法包括向所述场所施用控制杂草量的根据权利要求11至13中任一项所述的组合物。
15.如权利要求1所定义的具有式(I)的化合物作为除草剂的用途。
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