CN114144409A - 取代的哒嗪酮作为除草剂 - Google Patents
取代的哒嗪酮作为除草剂 Download PDFInfo
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- CN114144409A CN114144409A CN202080051175.9A CN202080051175A CN114144409A CN 114144409 A CN114144409 A CN 114144409A CN 202080051175 A CN202080051175 A CN 202080051175A CN 114144409 A CN114144409 A CN 114144409A
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- Prior art keywords
- alkyl
- radical
- alkoxy
- haloalkyl
- compound
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims description 22
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 189
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 21
- TVKFDBOFBKXOQT-UHFFFAOYSA-N 5-phenyl-1h-pyridazin-6-one Chemical class O=C1NN=CC=C1C1=CC=CC=C1 TVKFDBOFBKXOQT-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 C3-C6Cycloalkyl radical Chemical class 0.000 claims description 167
- 150000003254 radicals Chemical class 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 18
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 12
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 12
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 11
- 238000006467 substitution reaction Methods 0.000 claims description 11
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 150000002790 naphthalenes Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 9
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000000575 pesticide Substances 0.000 claims description 9
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 6
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 6
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 6
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 6
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 6
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 3
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 36
- GXZLRCBECYMKCZ-UHFFFAOYSA-N 5-phenylpyridazine-3,4-dione Chemical class C1(=CC=CC=C1)C=1C(C(N=NC=1)=O)=O GXZLRCBECYMKCZ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 244000045561 useful plants Species 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 35
- 235000019439 ethyl acetate Nutrition 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000003054 catalyst Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 150000002148 esters Chemical group 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 239000002585 base Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 23
- 238000011065 in-situ storage Methods 0.000 description 23
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 19
- 230000003197 catalytic effect Effects 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 229910052801 chlorine Inorganic materials 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- 229910052763 palladium Inorganic materials 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 11
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 10
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 241000894007 species Species 0.000 description 10
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 229920001213 Polysorbate 20 Polymers 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 8
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 8
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 7
- 244000237956 Amaranthus retroflexus Species 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 244000038559 crop plants Species 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 description 6
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
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- 229960004394 topiramate Drugs 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
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-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
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical class C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- 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
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- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
- C07D237/16—Two oxygen atoms
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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Abstract
本发明涉及具有式(I)的除草剂经取代的苯基‑哒嗪‑二酮和经取代的苯基‑哒嗪酮衍生物,以及用于制备此类衍生物的方法和中间体。本发明进一步延伸到包含此类衍生物的除草组合物,以及此类化合物和组合物在有用植物的作物中控制不希望的植物生长的用途:特别地控制杂草如阔叶双子叶杂草的用途。
Description
本发明涉及具有式(I)的除草剂经取代的苯基-哒嗪-二酮和经取代的苯基-哒嗪酮衍生物,以及用于制备此类衍生物的方法和中间体。本发明进一步延伸到包含此类衍生物的除草组合物,以及此类化合物和组合物在有用植物的作物中控制不希望的植物生长的用途:特别地控制杂草如阔叶双子叶杂草的用途。
除草剂哒嗪酮是从WO 2009/086041已知的。此外,除草剂5/6元杂环基取代的哒嗪酮是从WO 2011/045271已知的。同时WO 2013/160126描述了吲哚基-哒嗪酮衍生物,这些衍生物展示出除草活性。
本发明是基于以下发现:具有式(I)的经取代的苯基-哒嗪-二酮和经取代的苯基-哒嗪酮衍生物展示了出人意料地良好的除草活性。
因此,在第一方面,提供了一种具有式(I)的化合物
或其盐或N-氧化物,其中,
R1选自由以下组成的组:C1-C4烷基、C3-C6环烷基、C3-C6烷氧基、C1-C2烷氧基-C1-C2烷基-、C2-C4烯基、C1-C4卤代烷基、氰基-C1-C4烷基、C2-C4卤代烯基、C2-C4炔基和C2-C4卤代炔基;
R2选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C3卤代烷氧基-C1-C3烷基-、C1-C6烷氧基、C1-C3烷氧基-C1-C3烷基、C1-C3烷氧基-C1-C3烷氧基-C1-C3烷基-、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C6羟基烷基-、C1-C6烷基羰基-、-S(O)mC1-C6烷基、氨基、C1-C6烷基氨基、C1-C6二烷基氨基、-C(C1-C3烷基)=N-O-C1-C3烷基和C2-C6卤代炔基;
G是氢、或C(O)R3;
R3选自由以下组成的组:C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷基-S-、C1-C6烷氧基、-NR4R5和任选地被一个或多个R6取代的苯基;
R4和R5各自独立地选自由以下组成的组:氢、C1-C6烷基、C1-C6烷氧基和C3-C6环烷基,或者R4和R5一起可以形成吗啉基环;并且,
R6选自由以下组成的组:卤素、氰基、硝基、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基以及C1-C3卤代烷氧基;
X和Y各自独立地是氢、C1-C3烷基、环丙基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基、或卤素;
D是经取代或未经取代的萘环体系,或包含1、2、3或4个独立地选自氧、氮和硫的杂原子的经取代或未经取代的8-10元二环饱和、部分饱和或不饱和的杂环体系,并且其中当D被取代时,其在至少一个环碳原子上被R8取代和/或在至少一个环氮原子上被R9取代;
每个R8独立地是氧、羟基、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6-环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基-C1-C3烷基、C1-C3卤代烷氧基-C1-C3烷基-、C1-C3烷氧基-C1-C3烷氧基-C1-C3烷基-、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C6羟基烷基-、C1-C6烷基羰基-、C1-C6卤代烷基羰基-、C3-C6环烷基羰基-、C1-C6烷基-S(O)m-、-S(O)m-C1-C6卤代烷基、-S(O)m-C3-C6环烷基、-O-S(O)2C1-C3烷基、-C1-C3烷基-S(O)m-C1-C6烷基、-C1-C3烷基-S(O)m-C1-C6卤代烷基、-C1-C3烷基-S(O)m-C3-C6环烷基、氰基-C1-C6-烷基-、-NR4R5、-C(C1-C3烷基)=N-O-C1-C3烷基、-C(S)NH2、C1-C6烷基氨基硫代羰基-、二(C1-C6烷基)氨基硫代羰基-、C3-C6-环烷基氨基-硫代羰基-S(O)2NH2、-S(O)2NHC(O)C1-C3烷基、C1-C6烷基氨基磺酰基-、二(C1-C6烷基)氨基磺酰基-、C3-C6-环烷基氨基-磺酰基-、-C(O)OH、-C(O)OC1-C6烷基、-C(O)NHS-(O)2C1-C6烷基、-C(O)NR4R5、-NR4C(O)NR4R5、C1-C6烷基羰基(C1-C6烷基)氨基-、C1-C6卤代烷基羰基氨基-、C1-C6卤代烷基羰基(C1-C6烷基)氨基-、C1-C6烷氧基羰基氨基-、C1-C6烷氧基羰基(C1-C6烷基)氨基-、C1-C6烷基磺酰基氨基-、C1-C6烷基磺酰基(C1-C6烷基)氨基-、C1-C6卤代烷基磺酰基氨基-、C1-C6卤代烷基磺酰基(C1-C6烷基)氨基-、C3-C6环烷基磺酰基氨基-、C3-C6环烷基磺酰基(C1-C6烷基)氨基-、C1-C6烷基氨基羰基氨基-、C1-C6烷基氨基羰基(C1-C6烷基)氨基、二(C1-C6烷基)氨基羰基氨基-、C1-C6卤代烷基氨基羰基氨基-、C1-C6卤代烷基氨基-羰基(C1-C6烷基)氨基、二(C1-C6卤代烷基)氨基羰基氨基-、二(C1-C6卤代烷基)氨基-羰基(C1-C6烷基)氨基-、羟基氨基-、羟基(C1-C6烷基)氨基、C1-C6烷氧基氨基、C1-C6烷氧基(C1-C6烷基)氨基、C1-C6卤代烷氧基氨基、C1-C6卤代烷氧基(C1-C6烷基)氨基、或选自由苯基环、5-6元杂芳基环和3-6元杂环基环组成的组的环体系,其中所述环体系被0至5个R16取代;
m是0、1或2的整数;
每个R9独立地是C1-C6烷基、C1-C6卤代烷基、羟基、C1-C4烷氧基、C1-C4烷硫基、C3-C6-环烷基、C1-C3烷氧基-C1-C3烷基、C1-C3卤代烷氧基-C1-C3烷基-、C1-C3烷氧基-C1-C3烷氧基-C1-C3烷基-、C1-C6羟基烷基-、-C1-C3烷基-S(O)m-C1-C6烷基、-C1-C3烷基-S(O)m-C1-C6卤代烷基、-C1-C3烷基-S(O)m-C3-C6环烷基、氰基-C1-C6-烷基-、或选自由苯基环、5-6元杂芳基环和3-6元杂环基环组成的组的环体系,其中所述环体系被0至5个R16取代;
每个R16独立地是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基;并且,
W是
其中
“a”表示与苯基-哒嗪酮/苯基-哒嗪二酮部分的附接点,
“b”表示与环D的附接点,
R10、R12、R14和R15各自独立地是氢、C1-C3烷基或C1-C3卤代烷基;或者R10和R12与它们所连接的碳原子一起形成C3-C6碳环;并且
R11和R13各自独立地是氢、卤素、C1-C3烷基、或C1-C3卤代烷基,其前提是当R11或R13之一是卤素、C1-C3烷基或C1-C3卤代烷基时,另一个是氢。
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,或其中存在多于一个不对称中心,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,所述对映异构体之一具有增强的生物活性。
类似地,在存在双取代烯烃的情况下,这些可以以E或Z形式或作为任何比例的二者的混合物而存在。
此外,具有式(I)的化合物可以与替代的互变异构形式处于平衡。例如,具有式(I-i)的化合物,即,具有式(I)的化合物(其中R2是氢并且G是氢),可以被绘为至少三种互变异构形式:
应当领会的是,所有互变异构形式(单一互变异构体或其混合物)、外消旋混合物和单一异构体被包括在本发明的范围内。
每个烷基部分单独或者作为较大基团(如烷氧基、烷硫基、烷氧基羰基、烷基羰基、烷氨基羰基或二烷氨基羰基等)的一部分可以是直链或支链的。典型地,所述烷基是例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、新戊基、或正己基。烷基通常是C1-C6烷基(除了在已经更狭窄地定义时),但优选地是C1-C4烷基或C1-C3烷基,并且更优选地是C1-C2烷基(如甲基)。
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。烯基或炔基部分典型地是C2-C4烯基或C2-C4炔基,更确切地说是乙烯基、烯丙基、乙炔基、炔丙基或丙-1-炔基。烯基与炔基部分能以任何组合包含一个或多个双和/或三键;但是优选地仅包含一个双键(对于烯基)或仅包含一个三键(对于炔基)。
优选地,术语环烷基是指环丙基、环丁基、环戊基或环己基。
在本说明书的背景下,术语“芳基”优选地意指苯基。如本文使用的,术语“杂芳基”意指包含至少一个环杂原子的单环或二环的芳香族环体系。优选地,单环环体系将包含1、2或3个环杂原子,并且二环环体系将包含1、2、3或4个环杂原子,每个杂原子独立地选自氮、氧和硫。
典型地,单环杂芳基环选自由以下组成的组:呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、或1,3,5-三嗪基环。
典型地,二环杂芳基环体系选自由以下组成的组:吲哚嗪、吲哚、异吲哚、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、嘌呤、4H-喹嗪、喹啉、异喹啉、噌啉、酞嗪、喹喔啉、1-8-萘啶、或蝶啶环体系。
杂环基以及杂环(单独的或作为更大基团(如杂环基-烷基-)的一部分)是包含至少一个杂原子的环体系并且可以是处于单环或双环形式,并且可以是部分饱和或完全饱和的。优选地,杂环基将包含最多达两个杂原子,这些杂原子将优选地选自氮、氧以及硫。杂环基团的实例包括氧杂环丁烷基、硫杂环丁烷基、氮杂环丁烷基以及7-氧杂-双环[2.2.1]庚-2-基。包含单个氧原子作为杂原子的杂环基是最优选的。
卤素(或卤代)涵盖了氟、氯、溴或碘。所述卤素对应地应用于其他定义背景下的卤素,如卤代烷基或卤代苯基。
具有从1至6个碳原子链长的卤代烷基是,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、七氟正丙基以及全氟正己基。
烷氧基优选地具有从1至6个碳原子的链长。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或戊氧基或己氧基异构体,优选地甲氧基和乙氧基。还应当理解的是,两个烷氧基取代基可以存在于相同碳原子上。
卤代烷氧基是,例如氟甲氧基、二氟甲氧基、三氟甲氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、2-氟乙氧基、2-氯乙氧基、2,2-二氟乙氧基或2,2,2-三氯乙氧基,优选地是二氟甲氧基、2-氯乙氧基或三氟甲氧基。
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,优选地是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,优选地是甲基磺酰基或乙基磺酰基。
基团Q
本发明还包括农艺学上可接受的盐,具有式(I)的化合物可以与胺(例如氨、二甲胺和三乙胺)、碱金属和碱土金属碱或季铵盐碱形成这些盐。在用作成盐物的碱金属和碱土金属氢氧化物、氧化物、醇化物以及碳酸氢盐和碳酸盐之中,强调的是锂、钠、钾、镁和钙的氢氧化物、醇化物、氧化物以及碳酸盐,但尤其是钠、镁和钙的那些。还可以使用对应的三甲基锍盐。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。
R1、R2、R3、R4、R5、R6、R8、R9、R10、R11、R12、R13、R14、R15、W、D、G、X、Y、Z和m的优选值是如以下列出的,并且根据本发明的具有式(I)的化合物可以包括所述值的任何组合。技术人员将理解,用于任何指定组的实施例的值可以与用于任何其他组的实施例的值组合,其中此类组合不相互排斥。
优选地,R1选自由以下组成的组:甲基、乙基、丙基(具体地是正丙基或环丙基)、炔丙基或C1卤代烷基。更优选地,R1是甲基、乙基、环丙基、炔丙基或C1氟烷基。还更优选地,R1是甲基、乙基、环丙基或炔丙基。最优选地,R1是甲基。
优选地,R2选自由以下组成的组:氢、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C3烷氧基-C1-C3烷基、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基和C2-C6卤代炔基。更优选地,R2选自由以下组成的组:氯、氟、甲基、乙基、环丙基、三氟甲基和甲氧基甲基;还更优选地,氯、环丙基、三氟甲基或甲基;最优选地,氯或甲基。在本发明的一组实施例中,R2是氢。在另外一组实施例中,R2是环丙基;在第三组实施例中,R2是甲基,在第四组实施例中,R2是三氟甲基,并且在第五组实施例中,R2是氯。如本文所述,G可以是氢或–C(O)-R3,并且R3选自由以下组成的组:C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷基-S-、C1-C6烷氧基、-NR4R5以及任选地被一个或多个R6取代的苯基。如本文所定义的,R4和R5各自独立地选自由以下组成的组:氢、C1-C6烷基、C1-C6烷氧基-和C3-C6环烷基;或者它们可以一起形成吗啉基环。优选地,R4和R5各自独立地选自由以下组成的组:甲基、乙基、丙基、甲氧基、乙氧基和丙氧基。R6选自由以下组成的组:卤素、氰基、硝基、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基以及C1-C3卤代烷氧基。优选地,R6选自由以下组成的组:卤素、甲基、乙基、三氟甲基、甲氧基和乙氧基。
优选地,R3是C1-C4烷基、C2-C3烯基、C2-C3炔基、C1-C4烷氧基、或-NR4R5,其中R4和R5一起形成吗啉基环。更优选地,R3是异丙基、叔丁基、甲基、乙基、炔丙基、甲氧基、乙氧基或叔丁氧基
在一组实施例中,G是氢或-C(O)-R3,其中R3是C1-C4烷基、C2-C3烯基、C2-C3炔基或-C1-C3烷氧基。在另外一组实施例中,G是氢或-C(O)-R3,其中R3是异丙基、叔丁基、甲基、乙基、炔丙基或甲氧基。然而,特别优选的是,G是氢、或-C(O)-R3,其中R3是异丙基。
X优选地是氢、卤素、或C1卤代烷基,更优选地是氢、氟、氯、溴、或C1氟烷基并且还更优选地是氢、氟、氯或三氟甲基。在一组实施例中,优选的是,相对于哒嗪酮/哒嗪二酮部分(基团Q),X是在邻位(6位)。特别优选的是,X是氟、氯或C1-卤代烷基(特别是C1氟烷基)并且相对于哒嗪酮/哒嗪二酮部分(基团Q)是在邻位(6位)。最优选地,X是氟并且相对于哒嗪酮/哒嗪-二酮部分是在邻位(6位)。
Y优选地是氢、C1-C3烷基、环丙基、C1-C3卤代烷基、或卤素。更优选地,Y是氢、氯、氟、或溴。
在一组实施例中,优选的是相对于-W-D部分,Y是在邻位(3位)。在另外一组实施例中,相对于哒嗪酮/哒嗪二酮部分(基团Q),Y是在对位。
特别优选的是,相对于-W-D部分,Y是在邻位(3位),并且是卤素,特别是氯或氟;更优选氯。
在一组特别优选的实施例中,X是氟并且相对于哒嗪酮/哒嗪-二酮部分是在邻位(6位)并且Y是氯并且相对于-W-D部分是在邻位(3位)。
如本文所述,D是经取代或未经取代的萘环体系,或包含1、2、3或4个独立地选自氧、氮和硫的杂原子的经取代或未经取代的8-10元二环饱和、部分饱和或不饱和的杂环体系,并且其中当D被取代时,其在至少一个环碳原子上被R8取代和/或在适当时在环氮原子上被R9取代。在一组优选的实施例中,环体系D通过环碳原子连接到分子的剩余部分。
优选地,D是经取代或未经取代的萘环体系或是包含1、2、3或4个独立地选自氧、氮和硫的杂原子的经取代或未经取代的8-10-元二环杂环。更优选地,D是经取代(被至少一个R8和/或R9,如本文所述)或未经取代的萘、吲哚嗪、吲哚、异吲哚、吲哚啉、异吲哚啉、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并噁唑、苯并间二氧杂环戊烯、嘌呤、4H-喹嗪、喹啉、异喹啉、四氢喹啉、噌啉、酞嗪、喹喔啉、1-8-萘啶、蝶啶、1H-吡咯并[2,3-b]吡啶、咪唑并[1,2-a]吡嗪或1H-苯并三唑环体系。
甚至更优选地,D是经取代(被至少一个R8和/或R9,如本文所述)或未经取代的萘、吲哚嗪、吲哚、异吲哚、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并噁唑、嘌呤、4H-喹嗪、喹啉、异喹啉、四氢喹啉、噌啉、酞嗪、喹喔啉、1-8-萘啶、或蝶啶环体系。
更优选地,在此类实施例中,D是经取代(如本文所述)或未经取代的萘、喹啉、四氢喹啉、吲哚、或苯并噁唑环。
优选地,每个R8独立地是氧、羟基、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6-环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基-C1-C3烷基、C1-C3卤代烷氧基-C1-C3烷基-、C1-C3烷氧基-C1-C3烷氧基-C1-C3烷基-、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C6羟基烷基-、C1-C6烷基羰基-、C1-C6卤代烷基羰基-、C3-C6环烷基羰基-、C1-C6烷基-S(O)m-、-S(O)m-C1-C6卤代烷基、-S(O)m-C3-C6环烷基、-O-S(O)2C1-C3烷基、-C1-C3烷基-S(O)m-C1-C6烷基、-C1-C3烷基-S(O)m-C1-C6卤代烷基、-C1-C3烷基-S(O)m-C3-C6环烷基、氰基-C1-C6-烷基-、-NR4R5、-C(C1-C3烷基)=N-O-C1-C3烷基、-C(S)NH2、C1-C6烷基氨基硫代羰基-、二(C1-C6烷基)氨基硫代羰基-、C3-C6-环烷基氨基-硫代羰基-S(O)2NH2、-S(O)2NHC(O)C1-C3烷基、C1-C6烷基氨基磺酰基-、二(C1-C6烷基)氨基磺酰基-、C3-C6-环烷基氨基-磺酰基-、-C(O)OH、-C(O)OC1-C6烷基、-C(O)NHS-(O)2C1-C6烷基、-C(O)NR4R5、-NR4C(O)NR4R5、C1-C6烷基羰基(C1-C6烷基)氨基-、C1-C6卤代烷基羰基氨基-、C1-C6卤代烷基羰基(C1-C6烷基)氨基-、C1-C6烷氧基羰基氨基-、C1-C6烷氧基羰基(C1-C6烷基)氨基-、C1-C6烷基磺酰基氨基-、C1-C6烷基磺酰基(C1-C6烷基)氨基-、C1-C6卤代烷基磺酰基氨基-、C1-C6卤代烷基磺酰基(C1-C6烷基)氨基-、C3-C6环烷基磺酰基氨基-、C3-C6环烷基磺酰基(C1-C6烷基)氨基-、C1-C6烷基氨基羰基氨基-、C1-C6烷基氨基羰基(C1-C6烷基)氨基、二(C1-C6烷基)氨基羰基氨基-、C1-C6卤代烷基氨基羰基氨基-、C1-C6卤代烷基氨基-羰基(C1-C6烷基)氨基、二(C1-C6卤代烷基)氨基羰基氨基-、二(C1-C6卤代烷基)氨基-羰基(C1-C6烷基)氨基-、羟基氨基-、羟基(C1-C6烷基)氨基、C1-C6烷氧基氨基、C1-C6烷氧基(C1-C6烷基)氨基、C1-C6卤代烷氧基氨基、C1-C6卤代烷氧基(C1-C6烷基)氨基;
更优选地,每个R8独立地是氧、羟基、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C3卤代烷氧基-C1-C3烷基-、C1-C6烷氧基、C1-C3烷氧基-C1-C3烷基、C1-C3烷氧基-C1-C3烷氧基-C1-C3烷基-、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C6羟基烷基-、C1-C6烷基羰基-、C1-C6烷基-S(O)m-、氨基、C1-C6烷基氨基、C1-C6二烷基氨基、-C(C1-C3烷基)=N-O-C1-C3烷基或C2-C6卤代炔基。
甚至更优选地,每个R8独立地是羟基、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基。甚至还更优选地,每个R8独立地是C1-C3烷基、C1-C3卤代烷基、氯、氟、羟基、或C1-C3烷氧基。
优选地,每个R9独立地是C1-C4烷基、C1-C4卤代烷基、羟基、C1-C4烷氧基、或C1-C4烷硫基。更优选地,每个R9独立地是C1-C4烷基、或C1-C4烷氧基。甚至更优选地,每个R9独立地是C1-C4烷基。最优选地,每个R9是甲基。
m是0、1或2的整数。优选地,m是0或2。
W充当连接基部分,将环体系D连接到分子的剩余部分(即,连接到苯基-哒嗪酮/苯基-哒嗪二酮部分)。具有式(I)的化合物(其中连接基是W1和W3)是除草剂,而具有式(I)的化合物(其中连接基是W2)可以不仅是除草剂,还是可用于生产携带W1连接基的具有式(I)的化合物的中间体。因此,在一组实施例中,W是W1或W3(优选W1),而在第二组实施例中,W是W2。
优选地,R10、R11、R12和R13各自独立地选自氢或C1-C3烷基。在一组实施例中,R10、R11、R12和R13都是氢。
优选地,R14和R15各自独立地选自氢或C1-C3烷基。在一组实施例中,R14和R15都是氢。
在一组优选的实施例中,在具有式(I)的化合物中,
R1是甲基、乙基、环丙基、炔丙基或C1氟烷基;
R2是氯、环丙基、三氟甲基或甲基;
G是氢或-C(O)-R3,其中R3是异丙基、叔丁基、甲基、乙基、炔丙基、甲氧基、乙氧基、或叔丁氧基;
X是氟、氯或C1-卤代烷基并且相对于哒嗪酮/哒嗪-二酮部分是在邻位;
Y是氢、氯、氟或溴并且相对于-W-D部分是在邻位;
D是经取代或未经取代的萘环体系,或包含1、2、3或4个独立地选自氧、氮和硫的杂原子的经取代或未经取代的8-10元二环饱和、部分饱和或不饱和的杂环体系,并且其中当D被取代时,其在至少一个环碳原子上被R8取代和/或在至少一个环氮原子上被R9取代;
每个R8独立地是羟基、卤素、C1-C6烷基、C1-C6卤代烷基或C1-C6烷氧基;
每个R9独立地是C1-C4烷基、或C1-C4烷氧基;
W是W1;并且
R10、R11、R12和R13都是氢。
在一组甚至更优选的实施例中,在具有式(I)的化合物中,
R1是甲基;
R2是甲基;
G是氢或-C(O)-R3,其中R3是异丙基、叔丁基、甲基、乙基、炔丙基、甲氧基、乙氧基、或叔丁氧基;
X是氟并且相对于哒嗪酮/哒嗪-二酮部分是在邻位;
Y是氯并且相对于-W-D部分是在邻位;
D是经取代或未经取代的萘、吲哚嗪、吲哚、异吲哚、吲哚啉、异吲哚啉、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并噁唑、苯并间二氧杂环戊烯、嘌呤、4H-喹嗪、喹啉、异喹啉、四氢喹啉、噌啉、酞嗪、喹喔啉、1-8-萘啶、蝶啶、1H-吡咯并[2,3-b]吡啶、咪唑并[1,2-a]吡嗪或1H-苯并三唑环体系,并且其中当D被取代时,其在一个或两个环碳原子上被R8取代和/或在一个环氮原子上被R9取代;
每个R8独立地是C1-C3烷基、C1-C3卤代烷基、氯、氟、羟基、或C1-C3烷氧基;
R9是C1-C4烷基;
W是W1;并且
R10、R11、R12和R13都是氢。
下表1至4说明了本发明的具有式(I)的化合物的2752种具体实例。
本发明的除草化合物。用于描述X和Y的位置的编号系统仅为清楚起见而示出。
表1提供了688种具有如上示出的式(I)的化合物A-1.001至A-1.688,其中G是氢,W是-CH2-CH2-并且R1、R2、X、Y、D是如下表A中分别对于化合物编号1.001至1.688所定义的。
表A具有式(I)的化合物的R1、R2、X、Y和D的取代基定义
表2提供了688种具有如上示出的式(I)的化合物A-2.001至A-2.688,其中G是氢,W是(E)-CH=CH-并且R1、R2、X、Y、D是如上表A中分别对于化合物编号1.001至1.688所定义的。
表3提供了688种具有如上示出的式(I)的化合物A-3.001至A-3.688,其中G是-(C=O)iPr,W是-CH2-CH2-并且R1、R2、X、Y、D是如上表A中分别对于化合物编号1.001至1.288所定义的。
表4提供了688种具有如上示出的式(I)的化合物A-4.001至A-4.688,其中G是-(C=O)iPr,W是(E)-CH=CH-并且R1、R2、X、Y、D是如上表A中分别对于化合物编号1.001至1.288所定义的。
本发明的化合物可以根据以下方案制备,其中取代基R1、R2、R3、R4、R5、R6、R8、R9、R10、R11、R12、R13、R14、R15、R16、W、D、G、X、Y、Z和m具有(除非另外明确说明)在上文中所述的定义。
如在反应方案1中所示,可以由化合物(2)制备本发明的某些化合物(I-ii)。化合物(I-ii)是具有式(I)的化合物,其中W是-CH2-CH2-。
反应方案1
化合物(I-ii)可以通过化合物(2)与氢气在合适的溶剂[如四氢呋喃、甲醇、乙醇、乙酸或乙酸乙酯]中在合适的催化剂[如Pd/C、Pd/CaCO3、Rh/Al2CO3或海绵镍]存在下在-10℃与100℃之间的温度下的催化氢化来制备。
可替代地,化合物(I-ii)还可以通过在合适的溶剂中在合适的催化剂存在下在-10℃与100℃之间的温度下用合适的氢源处理通过化合物(2)的催化转移氢化来制备。合适的体系的实例是在Pd/C、Pd(OAc)2或Pd(OH)2/C存在下在二氯甲烷/水或二氯甲烷/甲醇混合物中的四羟基二硼(J.Am.Chem.Soc.[美国化学会志],2016,138,6107-6110)或在Pd/C存在下在乙醇中的1,4-二氢-2,6-二甲基-3,5-吡啶二甲酸二乙酯(Tetrahedron Letters[四面体通讯],2009,50,1026)。
可替代地,化合物(I-ii)还可以通过用由合适的前体原位生成的二酰亚胺在合适的溶剂中在-10℃与200℃之间的温度下还原制备。用于生成二酰亚胺的合适的试剂的实例包括任选地在合适的碱存在下经取代的芳基磺酰基酰肼,如2,4,6-三异丙基苯磺酰基酰肼。合适的碱的实例包括三乙胺、二异丙基乙胺、碳酸钾和碳酸钠。合适的溶剂包括四氢呋喃、1,4-二噁烷、乙酸乙酯、乙腈和二甲基甲酰胺。
如在反应方案2中所示,化合物(2)可以由化合物(3)和化合物(4)根据所述的铃木协议(Suzuki Protocol)或赫克协议(Heck Protocol)来制备。当采用铃木协议时,化合物(4)是有机硼化合物,如硼酸、硼酸酯或三氟硼酸钾盐。当采用赫克协议时,化合物(4)是苯乙烯。
反应方案2
铃木协议
化合物(2)可以通过在合适的碱和合适的催化剂存在下在合适的溶剂中在10℃与150℃之间的温度下用化合物(4)处理化合物(3)来制备。合适的碱的实例是碳酸钾、磷酸钾、碳酸钠、碳酸氢钠和氟化钾。合适的催化剂的实例是1,1’-双(二苯基膦基)二茂铁]二氯钯(II)二氯甲烷络合物[PdCl2(dppf).DCM]、四(三苯基膦)钯(0)[Pd(PPh3)4]、以及由乙酸钯(II)和三苯基膦的混合物原位形成的催化体系。合适的溶剂的实例是水、1,4-二噁烷、2-甲基四氢呋喃、四氢呋喃、乙腈和甲苯。许多化合物(4)是可商购的[如4,4,5,5-四甲基-2-[(E)-2-(2-萘基)乙烯基]-1,3,2-二氧杂环戊硼烷]或者可以通过已知的方法制得。在铃木协议中具有特定效用的化合物(3)的实例是异丁酰酯(3-i),其中G是异丁酰基。
技术人员将理解,铃木协议的条件易于裂解酯基,使得反应方案2也可以描述以下反应,在所述反应中起始材料(3)含有酯部分[使得G为酰基],但产物(2)不含[使得G为氢]。
赫克协议
化合物(2)可以通过在合适的碱和合适的催化剂存在下在10℃与150℃之间的温度下用化合物(4)处理化合物(3)来制备。可以任选地包括额外的溶剂。合适的碱的实例是三乙胺、吗啉、N-甲基吗啉、二异丙基乙胺和吡啶。合适的催化剂的实例是四(三苯基膦)钯(0)[Pd(PPh3)4]、由乙酸钯(II)和三苯基膦的混合物原位形成的催化体系、由三(二亚苄基丙酮)二钯(0)和三叔丁基鏻四氟硼酸盐的混合物原位形成的催化体系以及由环钯配合物预催化剂如氯[(三叔丁基膦)-2-(2-氨基联苯基)]钯(II)原位形成的催化体系。任选的额外的溶剂的实例是1,4-二噁烷、四氢呋喃、乙腈和甲苯。许多化合物(4)是可商购的[如2-乙烯基萘]或者可以通过已知的方法制得。在赫克协议中具有特定效用的化合物(3)的实例是异丁酰酯(3-i),其中G是异丁酰基。
如在反应方案3中所示,可以由化合物(5)制备化合物(3-i)。
反应方案3
化合物(3-i)可以通过在合适的溶剂[如二氯甲烷、乙腈或甲苯]中在合适的碱[如三乙胺、二异丙基乙胺或吡啶]存在下在-10℃与60℃之间的温度下用异丁酰氯处理化合物(5)来制备。可以任选地包括催化剂[如4-(二甲基氨基)吡啶]。
如在反应方案4中所示,化合物(5)可以由化合物(6)通过在溶剂[如乙腈、N,N-二甲基甲酰胺或甲苯]中在50℃与200℃之间的温度下加热化合物(6)与碱(如1,8-二氮杂二环[5.4.0]十一碳-7-烯、六甲基二硅氮烷钠或六甲基二硅氮烷锂)来制备。可以使用常规加热或微波加热。
反应方案4
如在反应方案5中所示,化合物(6)可以由苯乙酸(7)制备。
反应方案5
关于反应方案5,肼(8)的实例是甲基肼,并且酮酯(10)的实例是丙酮酸乙酯。腙(9)的实例是(2E/Z)-2-(甲基肼叉)丙酸乙酯,根据PCT专利申请WO 2016/008816中描述的方法制备。苯乙酸(7)的实例是(2-溴-6-氟-苯基)乙酸,其可以根据反应方案10来合成。苯乙酸(7)的另外的实例是(2-溴-3-氯-6-氟-苯基)乙酸,其可以根据反应方案11来合成。
本发明的某些化合物(I-iii)可以由化合物(11)(如在反应方案6中所示)或化合物(I-iv)(如在反应方案12中所示)制备。化合物(I-iii)是具有式(I)的化合物,其中W是-CH2-CH2-并且G是氢。
反应方案6
化合物(I-iii)可以通过在溶剂[如乙腈、N,N-二甲基甲酰胺或甲苯]中在50℃与200℃之间的温度下加热化合物(11)与碱(如1,8-二氮杂二环[5.4.0]十一碳-7-烯、六甲基二硅氮烷钠或六甲基二硅氮烷锂)来制备。可以使用常规加热或微波加热。
如在以下反应方案7中所示,可以由化合物(12)制备化合物(11)。
反应方案7
如在反应方案8中所示,可以由化合物(13)制备化合物(12)。许多化合物(13)是可商购的[如2-苯基乙酸甲酯和2-(2-氟苯基)乙酸甲酯]。
反应方案8
关于反应方案8,可以根据反应方案9来制备正膦(15)。
反应方案9
关于反应方案9,合适的碱的实例是氢化钠、六甲基二硅氮烷钠和叔丁醇钾。化合物(16)是亲电体,其中LG是离去基团[如氯化物、溴化物、碘化物、甲苯磺酸酯或甲磺酸酯]。许多化合物(16)是可商购的[如4-氯苄基溴或2-氯-5-氯甲基噻唑]。
反应方案10
关于反应方案10,可以如Lundgren等人JACS 2016,138,13826-13829中所述的制备(2-溴-6-氟-苯基)乙酸乙基酯。
反应方案11
关于反应方案11,2-溴-1-氯-4-氟-苯是可商购的。
反应方案12
化合物(I-iii)可以通过以下方式制备:在水和合适的溶剂[如甲醇、乙醇或四氢呋喃]的混合物中用金属氢氧化物[如氢氧化钠、氢氧化锂或氢氧化钾]处理化合物(I-iv);或在0℃与100℃之间的温度下在醇溶剂[如甲醇或乙醇]中用金属碳酸盐[如碳酸钠或碳酸钾]处理化合物(I-iv)。化合物(I-iv)是具有式(I)的化合物,其中W是-CH2-CH2-并且G是C(O)R3。
如在反应方案13中所示,化合物(2)可以由化合物(14)和化合物(15)根据所述的铃木协议或赫克协议来制备。当采用铃木协议时,化合物(14)是有机硼化合物,如硼酸、硼酸酯或三氟硼酸钾盐并且化合物(15)是卤化物或拟卤化物化合物,如氯化物、溴化物、碘化物或三氟甲磺酸盐。当采用赫克协议时,化合物(14)是苯乙烯并且化合物(15)是卤化物或拟卤化物化合物,如氯化物、溴化物、碘化物或三氟甲磺酸盐。
反应方案13
铃木协议
化合物(2)可以通过在合适的碱和合适的催化剂存在下在合适的溶剂中在10℃与150℃之间的温度下用化合物(15)处理化合物(14)来制备。合适的碱的实例是碳酸钾、磷酸钾、碳酸钠、碳酸氢钠和氟化钾。合适的催化剂的实例是1,1’-双(二苯基膦基)二茂铁]二氯钯(II)二氯甲烷络合物[PdCl2(dppf).DCM]、四(三苯基膦)钯(0)[Pd(PPh3)4]、以及由乙酸钯(II)和三苯基膦的混合物原位形成的催化体系。合适的溶剂的实例是水、1,4-二噁烷、2-甲基四氢呋喃、四氢呋喃、乙腈和甲苯。许多化合物(15)是可商购的或者可以通过已知的方法制得。在铃木协议中具有特定效用的化合物(14)的实例是异丁酰酯(14-i),其中G是异丁酰基。
技术人员将理解,铃木协议的条件易于裂解酯基,使得反应方案13也可以描述以下反应,在所述反应中起始材料(14)含有酯部分[使得G为酰基],但产物(2)不含[使得G为氢]。
赫克协议
化合物(2)可以通过在合适的碱和合适的催化剂存在下在10℃与150℃之间的温度下用化合物(15)处理化合物(14)来制备。可以任选地包括额外的溶剂。合适的碱的实例是三乙胺、吗啉、N-甲基吗啉、二异丙基乙胺和吡啶。合适的催化剂的实例是四(三苯基膦)钯(0)[Pd(PPh3)4]、由乙酸钯(II)和三苯基膦的混合物原位形成的催化体系、由三(二亚苄基丙酮)二钯(0)和三叔丁基鏻四氟硼酸盐的混合物原位形成的催化体系以及由环钯配合物预催化剂如氯[(三叔丁基膦)-2-(2-氨基联苯基)]钯(II)原位形成的催化体系。任选的额外的溶剂的实例是1,4-二噁烷、四氢呋喃、乙腈和甲苯。许多化合物(15)是可商购的或者可以通过已知的方法制得。在赫克协议中具有特定效用的化合物(14)的实例是异丁酰酯(14-i),其中G是异丁酰基。
如在反应方案14中所示,可以由化合物(3)和化合物(16)制备化合物(14-ii),其中J是有机硼物种,如硼酸酯。
反应方案14
化合物(14-ii)可以通过在合适的碱和合适的催化剂存在下在10℃与150℃之间的温度下用化合物(16)处理化合物(3)来制备。可以任选地包括额外的溶剂。合适的碱的实例是三乙胺、吗啉、N-甲基吗啉、二异丙基乙胺和吡啶。合适的催化剂的实例是四(三苯基膦)钯(0)[Pd(PPh3)4]、由乙酸钯(II)和三苯基膦的混合物原位形成的催化体系和由三(二亚苄基丙酮)二钯(0)和三叔丁基鏻四氟硼酸盐的混合物原位形成的催化体系。任选的额外的溶剂的实例是1,4-二噁烷、四氢呋喃、乙腈和甲苯。许多化合物(16)是可商购的,如乙烯基硼酸MIDA酯或乙烯基硼酸频哪醇酯,或者可以通过已知的方法制得。在赫克协议中具有特定效用的化合物(3)的实例是异丁酰酯(3-i),其中G是异丁酰基。
反应方案15
如在以上反应方案15中所示,可以由化合物(3)制备化合物(14-iii)(其中J是氢)。
化合物(14-iii)可以通过任选地在合适的碱存在下,在合适的催化剂存在下,在10℃与150℃之间的温度下在合适的溶剂中用三丁基(乙烯基)锡烷处理化合物(3)来制备。任选的碱的实例是三乙胺、吗啉、N-甲基吗啉、二异丙基乙胺和吡啶。合适的催化剂的实例是1,1’-双(二苯基膦基)-二茂铁]二氯钯(II)二氯甲烷络合物[PdCl2(dppf).DCM]、四(三苯基膦)钯(0)[Pd(PPh3)4]、由乙酸钯(II)和三苯基膦的混合物原位形成的催化体系、由三(二亚苄基丙酮)二钯(0)和三叔丁基鏻四氟硼酸盐的混合物原位形成的催化体系以及由环钯配合物预催化剂如氯[(三叔丁基膦)-2-(2-氨基联苯基)]钯(II)原位形成的催化体系。合适的溶剂的实例是1,4-二噁烷、四氢呋喃、乙腈和甲苯。具有特定效用的化合物(3)的实例是异丁酰酯(3-i),其中G是异丁酰基。
如在反应方案16中所示,可以由化合物(3)通过薗头(Sonogashira)反应制备化合物(18)。
反应方案16
化合物(18)可以通过在合适的碱和一种或多种合适的催化剂存在下在10℃与150℃之间的温度下用化合物(17)处理化合物(3)来制备。任选地,可以添加额外的溶剂。合适的碱的实例是三乙胺、吗啉、N-甲基吗啉、二异丙胺、二异丙基乙胺和吡啶。合适的催化剂的实例是双(三苯基膦)钯(II)二氯化物[Pd(PPh3)Cl2]、由乙酸钯(II)和三苯基膦的混合物原位形成的催化体系、由三(二亚苄基丙酮)二钯(0)和三叔丁基鏻四氟硼酸盐的混合物原位形成的催化体系以及由环钯配合物预催化剂如氯[(三叔丁基膦)-2-(2-氨基联苯基)]钯(II)原位形成的催化体系。任选地还可以添加铜催化剂,如碘化铜(I)。合适的额外的溶剂的实例是1,4-二噁烷、四氢呋喃、乙腈、甲苯和N,N-二甲基甲酰胺。具有特定效用的化合物(3)的实例是异丁酰酯(3-i),其中G是异丁酰基。
技术人员将理解,薗头反应的条件易于裂解酯基,使得反应方案16也可以描述以下反应,在所述反应中起始材料(3)含有酯部分[使得G为酰基],但产物(18)不含[使得G为氢]。
如在反应方案17中所示,化合物(19)可以由化合物(3)和化合物(20)通过铃木反应制备,其中化合物(20)是合适的有机硼物种,如硼酸、硼酸酯或三氟硼酸钾盐。
反应方案17
化合物(19)可以通过在合适的碱和合适的催化剂存在下在合适的溶剂中在10℃与150℃之间的温度下用化合物(20)处理化合物(3)来制备。合适的碱的实例是碳酸钾、磷酸钾、碳酸钠、碳酸氢钠和氟化钾。合适的催化剂的实例是1,1’-双(二苯基膦基)二茂铁]二氯钯(II)二氯甲烷络合物[PdCl2(dppf).DCM]、由三(二亚苄基丙酮)二钯(0)和三叔丁基鏻四氟硼酸盐的混合物原位形成的催化体系、由三(二亚苄基丙酮)二钯(0)和三环己基膦的混合物原位形成的催化体系、由环钯配合物预催化剂如氯[(三叔丁基膦)-2-(2-氨基联苯基)]钯(II)原位形成的催化体系、以及由环钯配合物预催化剂如氯[(三环己基膦)-2-(2’-氨基联苯基)]钯(II)原位形成的催化体系。合适的溶剂的实例是水、1,4-二噁烷、2-甲基四氢呋喃、四氢呋喃、乙腈和甲苯。一些化合物(20)是可商购的或者可以通过已知的方法制得(参见例如Org.Process Res.Dev.[有机过程研究与发展],2012,16,87-95中描述的方法)。在铃木反应中具有特定效用的化合物(3)的实例是苄基醚(3-ii),其中G是苄基。
反应方案18
化合物(I9-ii)可以通过化合物(19-i)与氢气在合适的溶剂[如四氢呋喃、甲醇、乙醇、乙酸或乙酸乙酯]中在合适的催化剂[如Pd/C、Pd/CaCO3、Rh/Al2CO3或海绵镍]存在下在-10℃与100℃之间的温度下的催化氢化来制备。
如在反应方案19中所示,可以由化合物(21)制备本发明的某些化合物(I-ii)。化合物(I-ii)是具有式(I)的化合物,其中W是-CH2-CH2-。
反应方案19
化合物(I-ii)可以通过在合适的碱和合适的催化剂存在下在合适的溶剂中在10℃与150℃之间的温度下用化合物(15)处理化合物(21)(其中[B]可以是三烷基硼烷、烷基硼酸、烷基硼酸酯或烷基三氟硼酸钾盐)来制备。合适的碱的实例是碳酸钾、磷酸钾、碳酸钠、碳酸铯、碳酸氢钠和氟化钾。合适的催化剂的实例是1,1’-双(二苯基膦基)二茂铁]-二氯钯(II)二氯甲烷络合物[PdCl2(dppf).DCM]、[1,3-双(2,6-二-3-戊基苯基)咪唑-2-亚基](3-氯吡啶基)二氯钯(II)[Pd-PEPPSITM-IPent]、由环钯配合物预催化剂如氯(2-二环己基膦基-2’,6’-二异丙氧基-1,1’-联苯基)[2-(2’-氨基-1,1’-联苯基)]钯(II)[RuPhos-Pd-G2]原位形成的催化体系、[二环己基[2’,4’,6’-三(1-甲基乙基)[1,1’-联苯基]-2-基]膦](甲烷磺酸基-κO)[2’-(甲基氨基-κN)[1,1’-联苯基]-2-基-κC]钯[XPhos-Pd-G4]、以及[(4-(N,N-二甲基氨基)苯基)二-叔丁基膦](甲烷磺酸基-κO)[2’-(甲基氨基-κN)[1,1’-联苯基]-2-基-κC]钯[APhos-Pd-G4]。合适的溶剂的实例是水、1,4-二噁烷、2-甲基四氢呋喃、四氢呋喃、乙腈和甲苯。许多化合物(15)是可商购的或者可以通过已知的方法制得。在铃木协议中具有特定效用的化合物(21)的实例是异丁酰酯(21-i),其中G是异丁酰基。
技术人员将理解,铃木协议的条件易于裂解酯基,使得反应方案19也可以描述以下反应,在所述反应中起始材料(21)含有酯部分[使得G为酰基],但产物(I-ii)不含[使得G为氢]。
反应方案20
化合物(21)可以通过在合适的溶剂中任选地添加合适的催化剂的情况下在0℃与100℃之间的温度下使用合适的硼氢化试剂(22)进行烯烃(14-iii)的硼氢化来制备。硼氢化试剂的实例包括硼烷、二氯硼烷、二溴硼烷、4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷[频哪醇硼烷]、1,3,2-苯并二氧杂戊硼烷[儿茶酚硼烷]或9-硼基双环[3.3.1]壬烷[9-BBN]。合适的溶剂的实例包括四氢呋喃、2-甲基四氢呋喃、1,4-二噁烷、2-甲氧基-2-甲基-丙烷[MTBE)和二乙醚。合适的催化剂的实例包括由双(1,5-环辛二烯)二铱(I)二氯化物[[Ir(COD)Cl]2]原位形成的催化体系、和4-二苯基磷烷基丁基(二苯基)磷烷[DPPB][J.Am.Chem.Soc.[美国化学会志],2004,126,9200-9201]。
在[B]是烷基硼酸酯时,这可以通过在合适的溶剂如二氯甲烷[DCM]中在0℃与40℃之间的温度下用甲基硼酸[MeB(OH)2]和三氟乙酸处理而转化为相应的硼酸[Org.Lett.[有机快报],2019,21,3048-3052]。在[B]是烷基硼酸或酯时,这可以通过在合适的溶剂如甲醇或丙酮中在0℃与40℃之间的温度下用氟氢化钾处理而转化为相应的烷基三氟硼酸钾盐。
根据本发明的化合物可以按未经修饰的形式用作除草剂,但它们通常以多种方式使用配制辅助剂(如载体、溶剂和表面活性物质)被配制成组合物。所述配制品可以处于不同的实体形式,例如,处于以下形式:撒粉剂、凝胶、可湿性粉剂、水可分散性颗粒剂、水可分散性片剂、泡腾压缩片剂、可乳化的浓缩物、微可乳化浓缩物、水包油乳剂、可流动油、水性分散体、油性分散体、悬乳剂、胶囊悬浮液、可乳化的颗粒剂、可溶性液体、水可溶性浓缩物(以水或水混溶性有机溶剂作为载体)、浸渍的聚合物膜或处于已知的其他形式,例如从Manual on Development and Use of FAO and WHO Specifications for Pesticides[关于杀有害生物剂的FAO和WHO标准的发展和使用的手册],联合国,第1版,二次修订(2010)中已知的。此类配制品可以直接使用或者使用前进行稀释。可以用例如水、液体肥料、微量营养素、生物有机体、油或溶剂来进行稀释。
可以通过例如将活性成分与配制辅助剂混合来制备这些配制品以便获得处于精细分散固体、颗粒、溶液、分散体或乳剂形式的组合物。所述活性成分还可以与其他辅助剂(如精细分散固体、矿物油、植物或动物来源的油、改性的植物或动物来源的油、有机溶剂、水、表面活性物质或其组合)来一起配制。
所述活性成分还可以被包含于非常精细的微胶囊中。微胶囊在多孔载体中含有活性成分。这使活性成分能以受控的量释放(例如,缓慢释放)到环境中。微胶囊通常具有从0.1至500微米的直径。它们包含的活性成分的量按重量计是胶囊重量的约从25%至95%。所述活性成分可以处于整体性的固体的形式、处于固体或液体分散体中的精细颗粒的形式或处于适合溶液的形式。包囊的膜可以包括例如天然的或合成的橡胶、纤维素、苯乙烯/丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯或化学改性的聚合物以及淀粉黄原酸酯、或本领域的技术人员已知的其他聚合物。可替代地,可以形成非常精细的微胶囊,其中活性成分在基础物质的固体基质中是以精细分散颗粒的形式被包含的,但这些微胶囊本身未经包裹。
适合于制备根据本发明的组合物的配制辅助剂本身是已知的。作为液体载体可以使用:水、甲苯、二甲苯、石油醚、植物油、丙酮、甲基乙基酮、环己酮、酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、碳酸丁烯酯、氯苯、环己烷、环己醇、乙酸烷基酯、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对-二乙基苯、二甘醇、松脂酸二乙二醇酯、二甘醇丁基醚、二甘醇乙基醚、二甘醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲基醚、双丙甘醇二苯甲酸酯、二丙二醇、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乳酸乙酯、乙二醇、乙二醇丁基醚、乙二醇甲基醚、γ-丁内酯、丙三醇、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸异戊基酯、乙酸异冰片基酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异亚丙基丙酮、甲氧基丙醇、甲基异戊基酮、甲基异丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、间二甲苯、正己烷、正辛胺、十八烷酸、辛胺乙酸酯、油酸、油烯基胺、邻二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸亚丙酯、丙二醇、丙二醇甲基醚、对-二甲苯、甲苯、磷酸三乙酯、三乙二醇、二甲苯磺酸、石蜡、矿物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇甲基醚、二乙二醇甲基醚、甲醇、乙醇、异丙醇以及更高分子量的醇,如戊醇、四氢呋喃醇、己醇、辛醇、乙二醇、丙二醇、甘油、N-甲基-2-吡咯烷酮等。
适合的固体载体是例如滑石、二氧化钛、叶蜡石黏土、硅石、凹凸棒石黏土、硅藻土、石灰石、碳酸钙、膨润土、钙蒙脱土、棉籽壳、小麦粉、大豆粉、浮石、木粉、经研磨的胡桃壳、木质素和类似的物质。
许多表面活性物质可以有利地用在固体和液体配制品两者中,尤其是在使用前可被载体稀释的那些配制品中。表面活性物质可以是阴离子的、阳离子的、非离子的或聚合的并且它们可以用作乳化剂、湿润剂或悬浮剂或用于其他目的。典型的表面活性剂包括,例如,烷基硫酸盐,如二乙醇铵硫酸月桂基酯;烷芳基磺酸盐,如十二烷基苯磺酸钙;烷基酚/氧化烯加成产物,如壬基酚乙氧基化物;醇/烯烃氧化物加成产物,如十三烷醇乙氧基化物;皂,例如硬脂酸钠;烷基萘磺酸盐,如二丁基萘磺酸钠;磺基琥珀酸盐的二烷基酯,如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季胺类,如十二烷基三甲基氯化铵;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及单烷基与二烷基磷酸酯的盐;以及还有描述在例如McCutcheon’s Detergents andEmulsifiers Annual[麦卡琴的洗涤剂和乳化剂年报],MC Publishing Corp.[MC出版公司],Ridgewood New Jersey[新泽西州里奇伍德](1981)中的其他物质。
可以用于杀有害生物配制品的另外的辅助剂包括结晶抑制剂、粘度改性剂、悬浮剂、染料、抗氧化剂、发泡剂、光吸收剂、混合助剂、消泡剂、络合剂、中和或改变pH的物质和缓冲液、腐蚀抑制剂、香料、湿润剂、吸收增强剂、微量营养素、增塑剂、助流剂、润滑剂、分散剂、增稠剂、防冻剂、杀微生物剂、以及液体和固体肥料。
根据本发明的组合物可以包括添加剂,所述添加剂包括植物或动物来源的油、矿物油、此类油的烷基酯或此类油与油衍生物的混合物。在根据本发明的组合物中的油添加剂的量通常是基于所述待施用的混合物的从0.01%到10%。例如,可以在喷雾混合物已经制备之后将油添加剂以所希望的浓度添加到喷雾罐中。优选的油添加剂包括矿物油或植物来源的油,例如菜籽油、橄榄油或葵花籽油;乳化的植物油;植物来源的油的烷基酯,例如甲基衍生物;或动物来源的油,如鱼油或牛脂。优选的油添加剂包括C8-C22脂肪酸的烷基酯,尤其是C12-C18脂肪酸的甲基衍生物,例如月桂酸、棕榈酸以及油酸的甲基酯(分别为月桂酸甲酯、棕榈酸甲酯和油酸甲酯)。许多油衍生物从Compendium of Herbicide Adjuvants[除草剂辅助剂纲要],第10版,Southern Illinois University[南伊利诺伊大学],2010中是已知的。
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括按重量计从0至25%的表面活性物质。这些本发明组合物总体上包括按重量计从0.1%至99%,尤其是按重量计从0.1%至95%的本发明的化合物以及按重量计从1%至99.9%的配制辅助剂,所述配制辅助剂优选地包括按重量计从0至25%的表面活性物质。而商业产品可以优选地被配制为浓缩物,最终使用者将通常使用稀释配制品。
施用率在宽范围之内变化并且取决于土壤的性质、施用方法、作物植物、待控制的有害生物、主要气候条件、以及受施用方法、施用时间和目标作物支配的其他因素。一般来讲,可以将化合物以从1l/ha至2000l/ha、尤其是从10l/ha到1000l/ha的比率施用。
优选的配制品可以具有以下组成(重量%):
可乳化的浓缩物:
活性成分:1%至95%、优选60%至90%
表面活性剂:1%至30%、优选5%至20%
液体载体:1%至80%、优选1%至35%
粉尘剂:
活性成分:0.1%至10%、优选0.1%至5%
固体载体:99.9%至90%、优选99.9%至99%
悬浮液浓缩物:
活性成分:5%至75%、优选10%至50%
水:94%至24%、优选88%至30%
表面活性剂:1%至40%、优选2%至30%
可湿性粉剂:
活性成分:0.5%至90%、优选1%至80%
表面活性剂:0.5%至20%、优选1%至15%
固体载体:5%至95%、优选15%至90%
颗粒剂:
活性成分:0.1%至30%、优选0.1%至15%
固体载体:99.5%至70%、优选97%至85%
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。
因此,具有式(I)的化合物可以与一种或多种其他除草剂组合使用以提供各种除草混合物。此类混合物的具体实例包括(其中“I”表示具有式(I)的化合物):-I+乙草胺;I+三氟羧草醚(包括三氟羧草醚-钠);I+苯草醚;I+莠灭净;I+氨唑草酮;I+氯氨基吡啶酸;I+杀草强;I+莠去津;I+beflubutamid-M;I+benquitrione;I+苄嘧磺隆(包括苄嘧磺隆-甲基);I+噻草平;I+二环吡喃酮;I+双丙氨膦;I+双草醚-钠;I+bixlozone;I+除草定;I+溴苯腈;I+丁草胺;I+氟丙嘧草酯;I+唑酮草酯(包括唑酮草酯-乙基);氯酯磺草胺(包括氯酯磺草胺-甲基);I+氯嘧磺隆(包括氯嘧磺隆-乙基);I+绿麦隆;I+氯磺隆;I+环庚草醚;I+氯酰草膦(clacyfos);I+烯草酮;I+炔草酸(包括炔草酸-炔丙基);I+异噁草酮;I+二氯吡啶酸;I+环吡拉尼(cyclopyranil);I+环吡瑞莫(cyclopyrimorate);I+环丙嘧磺隆;I+氰氟草酯(包括氰氟草酯-丁基);I+2,4-D(包括其胆碱盐和2-乙基己酯);I+2,4-DB;I+甜菜安;I+麦草畏(包括其铝;氨基丙基;双-氨基丙基甲基;胆碱;二氯丙;二甘醇胺;二甲胺;二甲基铵;钾和钠盐);I+双氯磺草胺;I+吡氟草胺;I+氟吡草腙;I+二甲草胺;I+精二甲吩草胺;I+敌草快二溴化物;I+敌草隆;I+epyrifenacil;I+丁氟消草;I+乙氧呋草黄;I+噁唑禾草灵(包括精噁唑禾草灵-乙基);I+异噁苯砜(fenoxasulfone);I+芬诺杀磺隆;I+fenquinotrione;I+四唑酰草胺;I+啶嘧磺隆;I+双氟磺草胺;I+氯氟吡啶酯(包括氯氟吡啶酯-苄基);I+吡氟禾草灵(包括精吡氟禾草灵-丁基);I+氟酮磺隆(包括氟酮磺隆-钠);I+氟噻草胺;I+唑嘧磺草胺;I+丙炔氟草胺;I+氟草隆;I+氟啶嘧磺隆(包括氟啶嘧磺隆-甲基-钠);I+氟草烟(包括氯氟吡氧乙酸(fluroxypyr-meptyl));I+氟磺胺草醚;I+甲酰胺磺隆;I+草铵膦(包括其铵盐);I+草甘膦(包括其联胺;异丙基铵和钾盐);I+氟氯吡啶酯(halauxifen)(包括氟氯吡啶酯-甲基);I+吡氟氯禾灵(包括吡氟氯禾灵-甲基);I+环嗪酮;I+hydantocidin;I+甲氧咪草烟;I+甲基咪草烟;I+灭草烟;I+咪草烟;I+三嗪茚草胺(indaziflam);I+碘甲磺隆(包括碘甲磺隆-甲基-钠);I+iofensulfuron(包括I+iofensulfuron-钠);I+碘苯腈;I+异丙隆;I+异噁唑草酮;I+lancotrione;I+MCPA;I+MCPB;I+高二甲四氯丙酸(mecoprop-P);I+甲基二磺隆(包括I+甲基二磺隆-甲基);I+甲基磺草酮;I+苯嗪草酮;I+吡草胺;I+异噁噻草醚(methiozolin);I+异丙甲草胺;I+磺草唑胺;I+嗪草酮;I+甲磺隆;I+敌草胺;I+烟嘧磺隆;I+达草灭;I+噁草酮;I+环氧嘧磺隆;I+乙氧氟草醚;I+二氯化百草枯;I+二甲戊乐灵;I+五氟磺草胺;I+苯敌草;I+毒莠定;I+唑啉草酯;I+丙草胺;I+氟嘧磺隆-甲基;I+扑草净;I+敌稗;I+喔草酯;I+丙嗪嘧磺隆(propyrisulfuron),I+戊炔草胺;I+苄草丹;I+氟磺隆;I+双唑草腈;I+吡草醚(包括吡草醚-乙基);I+磺酰草吡唑;I+哒草特;I+环酯草醚;I+pyrimisulfan,I+吡咯磺隆(pyroxasulfone);I+啶磺草胺;I+二氯喹啉酸;I+氯甲喹啉酸;I+喹禾灵(包括精喹禾灵-乙基和喹禾糠酯(quizalofop-P-tefuryl));I+砜嘧磺隆;I+嘧啶肟草醚;I+烯禾啶;I+西玛津;I+S-异丙甲草胺;I+甲磺草胺;I+磺酰磺隆;I+特丁噻草隆;I+特呋三酮;I+环磺酮;I+特丁津;I+特丁净;I+tetflupyrolimet;I+噻酮磺隆(thiencarbazone);I+噻吩磺隆;I+地芬纳噻(tiafenacil);I+托比利特(tolpyralate);I+苯吡唑草酮;I+三甲苯草酮;I+氟酮磺草胺(triafamone);I+野麦畏;I+醚苯磺隆;I+苯磺隆(包括苯磺隆-甲基);I+绿草定;I+三氟啶磺隆(包括三氟啶磺隆-钠);I+三气草嗦(trifludimoxazin);I+氟乐灵;I+氟胺磺隆;I+3-(2-氯-4-氟-5-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢嘧啶-1(2H)-基)苯基)-5-甲基-4,5-二氢异噁唑-5-甲酸乙酯;I+4-羟基-1-甲氧基-5-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮;I+4-羟基-1,5-二甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮;I+5-乙氧基-4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮;I+4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮;I+4-羟基-1,5-二甲基-3-[1-甲基-5-(三氟甲基)吡唑-3-基]咪唑烷-2-酮;I+(4R)1-(5-叔丁基异噁唑-3-基)-4-乙氧基-5-羟基-3-甲基-咪唑烷-2-酮;I+3-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]双环[3.2.1]辛烷-2,4-二酮;I+2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5-甲基-环己烷-1,3-二酮;I+2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]环己烷-1,3-二酮;I+2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5,5-二甲基-环己烷-1,3-二酮;I+6-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-2,2,4,4-四甲基-环己烷-1,3,5-三酮;I+2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5-乙基-环己烷-1,3-二酮;I+2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-4,4,6,6-四甲基-环己烷-1,3-二酮;I+2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-5-甲基-环己烷-1,3-二酮;I+3-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]双环[3.2.1]辛烷-2,4-二酮;I+2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-5,5-二甲基-环己烷-1,3-二酮;I+6-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-2,2,4,4-四甲基-环己烷-1,3,5-三酮;I+2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]环己烷-1,3-二酮;I+4-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-2,2,6,6-四甲基-四氢吡喃-3,5-二酮;I+4-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-2,2,6,6-四甲基-四氢吡喃-3,5-二酮;I+4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸(包括其农用化学上可接受的酯,例如,4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸甲酯、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸丙-2-炔酯和4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸氰基甲酯);I+3-乙基硫烷基-N-(1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺;I+3-(异丙基硫烷基甲基)-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺;I+3-(异丙基磺酰基甲基)-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺;I+3-(乙基磺酰基甲基)-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺;I+2-[[3-[[3-氯-5-氟-6-[3-甲基-2,6-二氧代-4-(三氟甲基)嘧啶-1-基]-2-吡啶基]氧基]乙酸乙酯;I+6-氯-4-(2,7-二甲基-1-萘基)-5-羟基-2-甲基-哒嗪-3-酮;I+1-[2-氯-6-(5-氯嘧啶-2-基)氧基-苯基]-4,4,4-三氟-丁-1-酮以及I+5-[2-氯-6-(5-氯嘧啶-2-基)氧基-苯基]-3-(二氟甲基)异噁唑。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The Pesticide Manual[杀有害生物剂手册],第十四版,British Crop Protection Council[英国作物保护委员会],2006中所提到的。
具有式(I)的化合物还可以在与其他农用化学品(如杀真菌剂、杀线虫剂或杀昆虫剂)的混合物中使用,这些农用化学品的实例在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)。
本发明的具有式(I)的化合物也可以与除草剂安全剂组合。优选的组合(其中“I”表示具有式(I)的化合物)包括:-I+解草嗪,I+解草酯(包括解草喹(cloquintocet-mexyl));I+环丙磺酰胺;I+二氯丙烯胺;I+解草唑(包括解草唑-乙基);I+解草啶;I+氟草肟;I+解草噁唑I+双苯噁唑酸(包括双苯噁唑酸-乙基);I+吡唑解草酸(包括吡唑解草酸-二乙基);I+metcamifen;I+N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺和I+解草腈。
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(包括双苯噁唑酸-乙基)、解草酯(包括解草喹)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处于酯或盐的形式,例如像在杀有害生物剂手册,第14版(BCPC),2006中所提到的。对解毒喹的提及还适用于锂、钠、钾、钙、镁、铝、铁、铵、季铵、锍或其鏻盐(如在WO 02/34048中披露的),并且对解草唑乙酯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。
这些混合物可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)的化合物与安全剂的对应混合物)。
本发明的具有式(I)的化合物作为除草剂是有用的。因此,本发明还包括用于控制不想要的植物的方法,包括向所述植物或包含它们的场所施用有效量的本发明化合物或含有所述化合物的除草组合物。’控制’意指杀死、减少或延迟生长或防止或减少发芽。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;出苗后;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到1000g/ha的比率施用。
通常通过喷洒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洒机,但是还可以使用其他方法如撒粉(针对粉末)、滴加或浸湿。
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))。通过基因工程方法而赋予对除草剂的耐受性的作物的实例包括例如草甘膦和草丁膦抗性的玉米品种,所述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其对有害昆虫的抗性的那些作物,例如Bt玉米(对欧洲玉米螟有抗性)、Bt棉花(对棉铃象鼻虫有抗性)以及还有Bt马铃薯(对科罗拉多甲虫有抗性)。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-451 878、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和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,如花卉或灌木。
本发明的具有式(I)的化合物和组合物通常可以用于控制多种单子叶和双子叶杂草物种。典型地可以被控制的单子叶物种的实例包括大穗看麦娘(Alopecurusmyosuroides)、野燕麦(Avena fatua)、车前臂形草(Brachiaria plantaginea)、旱雀麦(Bromus tectorum)、油莎草(Cyperus esculentus)、马唐(Digitaria sanguinalis)、稗草(Echinochloa crus-galli)、多年生黑麦草(Lolium perenn)、多花黑麦草(Loliummultiflorum)、黍稷(Panicum miliaceum)、一年生早熟禾(Poa annua)、狗尾草(Setariaviridis)、大狗尾草(Setaria faberi)和两色蜀黍(Sorghum bicolor)。可以被控制的双子叶物种的实例包括:苘麻、反枝苋、鬼针草、藜草、白苞猩猩草、猪殃殃、牵牛花、地肤、卷茎蓼、刺金午时花、新疆野生油菜、龙葵、繁缕、波斯婆婆纳和苍耳。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。
现在通过举例更详细地说明本发明的不同方面和实施例。应当理解的是,在不偏离本发明范围的情况下,可以对细节做出修改。
制备实例
实例1 2-甲基丙酸[5-[3-氯-6-氟-2-[2-(2-甲基-6-喹啉基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(A-3.034)的制备
1.1 3-烯丙基-2-溴-1-氯-4-氟-苯
将二异丙基氨基锂的溶液(在四氢呋喃中2M,3.6ml,7.2mmol)在N2下冷却至-78℃。在-78℃下,逐滴地添加2-溴-1-氯-4-氟-苯(1.0g,4.8mmol)在四氢呋喃中的溶液。将混合物在用烯丙基溴(0.3ml,5.7mmol)处理之前在同一温度下搅拌45分钟。将反应在-78℃下继续进行2h然后升温至室温。将反应用饱和NH4Cl(水性)淬灭并且用乙酸乙酯萃取。将有机物分离并保留,然后将其用盐水洗涤。将有机物经硫酸钠干燥并在减压下浓缩,以给出呈油状物的3-烯丙基-2-溴-1-氯-4-氟-苯(1.2g,100%)。
1H NMR(400MHz,CDCl3)δH:7.34-7.30(m,1H),7.01-6.96(m,1H),5.94-5.83(m,1H),5.10-5.00(m,2H),3.64-3.58(m,2H)。
1.2 2-(2-溴-3-氯-6-氟-苯基)乙酸
将3-烯丙基-2-溴-1-氯-4-氟-苯(15.0g,60.1mmol)于二氯甲烷(200mL)中的溶液在2颈烧瓶中冷却至-78℃。将一侧颈连接到包含KI的水溶液的阱上。将臭氧鼓泡通过所述溶液,直至起始材料被完全消耗(5小时)。将空气鼓泡通过所述溶液持续10分钟,以除去过量的臭氧。添加二甲基硫醚(44ml,601mmol),并将混合物升温至室温。将所述反应在室温下继续16h。
将混合物用盐水(2×100mL)洗涤,并保留有机层。将有机物经Na2SO4干燥、过滤并在减压下浓缩,以给出粗的2-(2-溴-3-氯-6-氟-苯基)乙醛(15.3g),将其不经进一步纯化用于下一步骤。
将粗的2-(2-溴-3-氯-6-氟-苯基)乙醛(15.3g,60.8mmol)溶于叔丁醇(92mL)和水(46mL)的混合物中,然后冷却至0℃。添加2-甲基丁-2-烯(64.5mL,608mmol)、磷酸二氢钠(34.6g,243mmol)和亚氯酸钠(16.5g,163mmol)。将混合物搅拌2h,然后用盐水(150mL)和2M盐酸(150mL)稀释。将混合物用乙酸乙酯(3×100mL)萃取。将合并的有机萃取物用饱和焦亚硫酸钠水溶液(100mL)洗涤,然后经Na2SO4干燥、过滤并在减压下浓缩以提供淡黄色固体。将粗固体溶解水(100mL)和2.0M NaOH(30mL)的混合物中。将水溶液用乙酸乙酯(100mL)洗涤并丢弃有机物。通过添加浓盐酸(20mL)将水层酸化,导致形成白色悬浮液。将混合物用乙酸乙酯(3×200mL)萃取。将合并的有机物用盐水洗涤、经Na2SO4干燥、过滤并蒸发,以提供呈白色固体的2-(2-溴-3-氯-6-氟-苯基)乙酸(8.0g,49%)。
1H NMR(400MHz,DMSO-d6)δH:12.79(br.s,1H),7.67-7.59(m,1H),7.39-7.31(m,1H),3.82(s,2H)。
1.3 2-(2-溴-3-氯-6-氟-苯基)-N-甲基-乙酰肼
向0℃下的2-(2-溴-3-氯-6-氟-苯基)乙酸(2.0g,7.5mmol)在二氯甲烷(20ml)中的搅拌溶液中添加N-(3-二甲基氨基丙基)-N’-乙基碳二亚胺盐酸盐[EDC.HCl](1.4g,9.0mmol),接着逐滴地添加甲基肼(0.4ml,7.5mmol)。将反应混合物的温度维持在0℃持续3h。然后将反应用水淬灭并萃取至二氯甲烷中。将有机物分离、用盐水洗涤并经Na2SO4干燥。在减压下浓缩给出粗的2-(2-溴-3-氯-6-氟-苯基)-N-甲基-乙酰肼(1.8g,81%),将其不经进一步纯化用于下一步骤。
1H NMR(400MHz,DMSO-d6)δH:7.59(dd,J=8.9和5.4,1H),7.30(t,J=8.9,1H),4.91(s,2H),4.10(br.s,2H),3.02(s,3H)。
1.4 2-{[2-(2-溴-3-氯-6-氟-苯基)-乙酰基]-甲基-亚肼基}-丙酸乙基酯
向2-(2-溴-3-氯-6-氟-苯基)-N-甲基-乙酰肼(1.8g,6.09mmol)在乙醇(5ml)中的搅拌溶液中逐滴地添加丙酮酸乙酯(0.7ml,6.7mmol)。将反应在80℃下加热4h。然后将反应混合物冷却至室温,并在减压下蒸发。将残余物通过硅胶柱色谱法(洗脱液:乙酸乙酯/己烷梯度)纯化,以给出呈灰白色固体的所希望的化合物2-{[2-(2-溴-3-氯-6-氟-苯基)-乙酰基]-甲基-亚肼基}-丙酸乙基酯(1.8g,75%)。
1H NMR(400MHz,CDCl3)δH:7.40-7.35(m,1H),7.04-6.98(m,1H),4.32(q,J=7.1,2H),4.24(s,2H),3.41(s,3H),2.32(s,3H),1.36(t,J=7.1,3H)。
1.5 4-(2-溴-3-氯-6-氟-苯基)-5-羟基-2,6-二甲基-哒嗪-3-酮
将2-{[2-(2-溴-3-氯-6-氟-苯基)-乙酰基]-甲基-亚肼基}-丙酸乙基酯(500mg,1.27mmol)溶解于乙腈(2.5ml)中并用1,8-二氮杂二环[5.4.0]十一碳-7-烯[DBU](0.47ml,3.2mmol)处理。使用微波辐射将混合物加热至125℃持续1h。然后将反应混合物在减压下蒸发。将残余物溶解于水中并用2N盐酸酸化至pH 1。将混合物用DCM萃取,将有机物分离并用盐水溶液洗涤。将有机溶液经Na2SO4干燥并在减压下浓缩以给出粗产物。将所述粗产物通过硅胶柱色谱法(洗脱液:乙酸乙酯/己烷梯度)纯化以给出呈灰白色固体的4-(2-溴-3-氯-6-氟-苯基)-5-羟基-2,6-二甲基-哒嗪-3-酮(340mg,77.1%)。
1.6 2-甲基丙酸[5-(2-溴-3-氯-6-氟-苯基)-1,3-二甲基-6-氧代-哒嗪-4-基]酯
向室温下的4-(2-溴-3-氯-6-氟-苯基)-5-羟基-2,6-二甲基-哒嗪-3-酮(1.4g,4.02mmol)在二氯甲烷(32ml)中的搅拌溶液中添加三乙胺(1.1ml,8.06mmol)、4-(二甲基氨基)吡啶[DMAP](49mg,0.40mmol)和异丁酰氯(0.6ml,4.83mmol)。
一旦判断完成,将反应用二氯甲烷和水稀释。将有机层分离、经Na2SO4干燥并在减压下浓缩以给出粗产物。将所述粗产物通过硅胶柱色谱法(洗脱液:乙酸乙酯/己烷梯度)纯化以给出2-甲基丙酸[5-(2-溴-3-氯-6-氟-苯基)-1,3-二甲基-6-氧代-哒嗪-4-基]酯(1.47g,87%)。
1H NMR(400MHz,CDCl3)δH:7.51-7.47(m,1H),7.10-7.05(m,1H),3.82(s,3H),2.60-2.55(m,1H),2.25(s,3H),1.02-0.98(m,6H)。
1.7 2-甲基-6-[(E)-2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)乙烯基]喹啉
将4,4,5,5-四甲基-2-乙烯基-1,3,2-二氧杂环戊硼烷(0.73mL,4.32mmol)和N,N-二异丙基乙胺(1.25mL,7.20mmol)添加到6-溴-2-甲基-喹啉(800mg,3.6mmol)和氯[(三叔丁基膦)-2-(2-氨基联苯基)]钯(II)(92mg,0.18mmol)在甲苯(14mL)中的搅拌溶液中。将反应混合物在氮气下加热至95℃持续4h。
完成后将反应混合物冷却至室温,然后通过过滤(用DCM洗脱)。将滤液在真空中浓缩,然后通过快速柱色谱法(二氧化硅,洗脱液:乙酸乙酯/异己烷梯度)纯化以给出2-甲基-6-[(E)-2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)乙烯基]喹啉(886mg,83%产率)。 1H NMR(400MHz,溶剂)δppm 1.34(s,12H)2.74(s,3H)6.29(d,J=18.46Hz,1H)7.26-7.29(m,1H)7.55(d,J=18.4Hz,1H)7.77(d,J=1.47Hz,1H)7.85-7.92(m,1H)7.94-7.99(m,1H)8.02(d,J=8.4Hz,1H)。
1.8 2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(2-甲基-6-喹啉基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(A-4.034)
将2-甲基丙酸[5-(2-溴-3-氯-6-氟-苯基)-1,3-二甲基-6-氧代-哒嗪-4-基]酯(1.03g,2.47mmol)、Cs2CO3(2.43g,7.40mmol)、2-甲基-6-[(E)-2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)乙烯基]喹啉(0.874g,2.96mmol)和Pd(dppf)Cl2.DCM(0.101g,0.123mmol)在1,4-二噁烷(21mL)和水(6mL)中的搅拌溶液在回流下加热。
16h后,将反应混合物在真空中浓缩以除去大部分的所述二噁烷,然后用水和EtOAc稀释。分离有机层并且用多个部分的EtOAc(2X)萃取水相。然后用2M HCl(水性)将水相的pH调节至pH 2,然后用另外部分的EtOAc萃取。
将粗产物通过快速柱色谱法(二氧化硅,洗脱液:乙酸乙酯/异己烷梯度)纯化以给出2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(2-甲基-6-喹啉基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(86mg,7%产率,A-4.034)和4-[3-氯-6-氟-2-[(E)-2-(2-甲基-6-喹啉基)乙烯基]苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(51mg,5%产率,A-2.034)。
1H NMR(400MHz,CDCl3)δppm 1.11(app t,J=7.1Hz,6H)2.23(s,3H)2.63-2.71(m,1H)2.74(s,3H)3.69(s,3H)6.81(d,J=16.4Hz,1H)7.04(t,J=8.7Hz,1H)7.15(d,J=16.5Hz,1H)7.27(s,1H)7.45(dd,J=8.9,5.07Hz,1H)7.63(d,J=1.7Hz,1H)7.75-7.81(m,1H)7.94(d,J=8.8Hz,1H)8.01(d,J=8.3Hz,1H)。
1H NMR(400MHz,CDCl3)δppm 2.24(s,3H)2.66(s,3H)3.66(s,3H)6.72(d,J=16.4Hz,1H)6.93-7.07(m,2H)7.26(s,1H)7.38(dd,J=8.9,5.14Hz,1H)7.55(d,J=1.7Hz,1H)7.66(dd,J=8.8,2.0Hz,1H)7.84(d,J=8.8Hz,1H)7.99(d,J=8.4Hz,1H)
1.9 2-甲基丙酸[5-[3-氯-6-氟-2-[2-(2-甲基-6-喹啉基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(A-3.034)
使2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(2-甲基-6-喹啉基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(56mg,0.12mmol,4.034)在3巴H2下在四氢呋喃(0.3mL)中在5%Pd/C催化剂(24mg)上经受催化氢化。
将残余物吸附到二氧化硅上并通过快速柱色谱法(二氧化硅,洗脱液:乙酸乙酯/异己烷)纯化以给出2-甲基丙酸[5-[3-氯-6-氟-2-[2-(2-甲基-6-喹啉基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(15mg,27%产率,A-3.034)以及进一步还原的产物的混合物(将其通过质量定向的反相制备型HPLC进一步纯化以给出2-甲基丙酸[5-[3-氯-6-氟-2-[2-(2-甲基-1,2,3,4-四氢喹啉-6-基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(6mg,11%产率,A-3.030))。
1H NMR(400MHz,CDCl3)δppm 0.97(dd,J=7.0,4.4Hz,6H)2.24(s,3H)2.47-2.57(m,1H)2.73(s,3H)2.79-3.09(m,4H)3.84(s,3H)7.00(t,J=8.6Hz,1H)7.25(d,J=8.3Hz,1H)7.49(app d,J=1.1Hz,3H)7.90(d,J=8.4Hz,1H)7.96(d,J=8.3Hz,1H)。
1H NMR(400MHz,CDCl3)δppm 0.96(dd,J=7.03,2.02Hz,6H)1.25(d,J=6.24Hz,3H)1.58-1.69(m,1H)1.90-1.98(m,1H)2.24(s,3H)2.54(dt,J=13.94,6.97Hz,1H)2.63-2.84(m,6H)3.39(td,J=6.51,3.12Hz,1H)3.83(s,3H)6.52(br d,J=6.48Hz,1H)6.72-6.79(m,2H)6.96(t,J=8.62Hz,1H)7.40(dd,J=8.80,5.14Hz,1H)。
实例2 4-[3-氯-6-氟-2-[2-(1H-吲哚-5-基)乙基]苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(A-1.021)的制备
2.1 5-苄氧基-4-(2-溴-3-氯-6-氟-苯基)-2,6-二甲基-哒嗪-3-酮
将苄基溴(0.19mL,1.58mmol)添加到4-(2-溴-3-氯-6-氟-苯基)-5-羟基-2,6-二甲基-哒嗪-3-酮(500mg,1.44mmol)和K2CO3(0.22g,1.58mmol)在丙酮(2.9mL)中的搅拌悬浮液中并且将混合物在回流下加热2h。
完成后将反应混合物冷却至室温,然后过滤(用丙酮洗脱)。将滤液在真空中浓缩,然后通过快速柱色谱法(二氧化硅,洗脱液:乙酸乙酯/异己烷梯度)纯化以给出5-苄氧基-4-(2-溴-3-氯-6-氟-苯基)-2,6-二甲基-哒嗪-3-酮(560mg,89%产率)。
1H NMR(400MHz,CDCl3)δppm 2.29(s,3H)3.77(s,3H)4.59-4.76(m,2H)7.09(dd,J=8.93,7.95Hz,1H)7.13-7.20(m,2H)7.29-7.36(m,3H)7.52(dd,J=8.93,5.38Hz,1H)。
2.2 2-[(E)-2-[2-(5-苄氧基-2,6-二甲基-3-氧代-哒嗪-4-基)-6-氯-3-氟-苯基]乙烯基]-6-甲基-1,3,6,2-二氧氮硼杂八环-4,8-二酮
将5-苄氧基-4-(2-溴-3-氯-6-氟-苯基)-2,6-二甲基-哒嗪-3-酮(1.00g,2.28mmol)、氯[(三叔丁基膦)-2-(2-氨基联苯基)]钯(II)(59mg,0.11mmol)、N,N-二异丙基乙胺(0.80mL,4.57mmol)和6-甲基-2-乙烯基-1,3,6,2-二氧氮硼杂八环-4,8-二酮(0.50g,2.74mmol)在THF(23mL)中的搅拌溶液在90℃下加热5h然后在70℃下加热另外16h。
将反应混合物冷却至室温,然后用DCM稀释并通过过滤,用另外部分的DCM洗脱。将滤液在真空中浓缩,然后通过快速柱色谱法(二氧化硅,洗脱液:乙酸乙酯/甲醇梯度)纯化以给出5-苄氧基-4-(2-溴-3-氯-6-氟-苯基)-2,6-二甲基-哒嗪-3-酮;2-[(E)-2-[2-(5-苄氧基-2,6-二甲基-3-氧代-哒嗪-4-基)-6-氯-3-氟-苯基]乙烯基]-6-甲基-1,3,6,2-二氧氮硼杂八环-4,8-二酮(904mg,74%产率)。
1H NMR(400MHz,CDCl3)δppm2.26(s,3H)2.79(s,3H)3.73(s,7H)4.60(s,2H)5.97(d,J=18.6Hz,1H)6.76(d,J=18.5Hz,1H)7.02(t,J=8.6Hz,1H)7.09(dd,J=6.7,3.00Hz,2H)7.29-7.34(m,3H)7.44(dd,J=8.9,5.1Hz,1H)。
2.3 5-苄氧基-4-[3-氯-6-氟-2-[(E)-2-(1H-吲哚-5-基)乙烯基]苯基]-2,6-二甲基-哒嗪-3-酮
向微波小瓶中添加2-[(E)-2-[2-(5-苄氧基-2,6-二甲基-3-氧代-哒嗪-4-基)6-氯-3-氟-苯基]乙烯基]-6-甲基-1,3,6,2-二氧氮硼杂八环-4,8-二酮(300mg,0.56mmol)、5-溴-1H-吲哚(163mg,0.84mmol)、Pd(dppf)Cl2.DCM(23mg,0.028mmol)和K3PO4.H2O(512mg,2.22mmol)。然后将小瓶加盖并用N2吹扫,然后添加THF(5.6mL)和水(0.2mL)。然后在微波辐射下,将反应混合物加热至90℃持续30min。
将反应混合物冷却至室温然后在水(20mL)与EtOAc(20mL)之间分配。分离有机层并且用EtOAc(2×20mL)萃取水层。将合并的有机物收集、干燥(MgSO4)、过滤并在真空中浓缩以给出粗产物。
将粗产物通过质量定向的反相制备型HPLC纯化以给出5-苄氧基-4-[3-氯-6-氟-2-[(E)-2-(1H-吲哚-5-基)乙烯基]苯基]-2,6-二甲基-哒嗪-3-酮(45mg,16%产率)。
1H NMR(400MHz,CDCl3)δppm2.20(s,3H)3.76(s,3H)4.70(d,J=5.3Hz,2H)6.53(t,J=2.1Hz,1H)6.78-6.86(m,1H)6.88-6.94(m,1H)7.01(t,J=8.6Hz,1H)7.12-7.17(m,2H)7.19(t,J=2.8Hz,1H)7.21-7.25(m,1H)7.29-7.35(m,4H)7.47(dd,J=8.9,5.3Hz,1H)7.55(s,1H)8.25-8.44(m,1H)。
2.4 4-[3-氯-6-氟-2-[2-(1H-吲哚-5-基)乙基]苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(A-1.021)
使5-苄氧基-4-[3-氯-6-氟-2-[(E)-2-(1H-吲哚-5-基)乙烯基]苯基]-2,6-二甲基-哒嗪-3-酮(45mg,0.09mmol)在3巴H2下在四氢呋喃(0.23mL)中在5%Pd/C催化剂(38mg×2)上经受催化氢化。
将残余物吸附到二氧化硅上并通过快速柱色谱法(二氧化硅,洗脱液:乙酸乙酯/异己烷)纯化以给出4-[3-氯-6-氟-2-[2-(1H-吲哚-5-基)乙基]苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(24mg,65%产率,A-1.021)。
1H NMR(400MHz,CDCl3)δppm 2.18(s,3H)2.70-2.96(m,4H)3.69(s,3H)6.44(ddd,J=3.0,2.0,0.7Hz,1H)6.78(dd,J=8.3,1.6Hz,1H)6.89(t,J=8.6Hz,1H)7.14-7.18(m,1H)7.18-7.26(m,2H)7.37(dd,J=8.8,5.14Hz,1H)8.21(br s,1H)。
实例3 4-[3-氯-6-氟-2-[2-(3-甲基苯并三唑-5-基)乙基]苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(1.343)的制备
3.1 2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(6-甲基-4,8-二氧代-1,3,6,2-二氧氮硼杂八环-2-基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯
将2-甲基-丙酸[5-(2-溴-3-氯-6-氟-苯基)-1,3-二甲基-6-氧代-哒嗪-4-基]酯(5.00g,11.97mmol,1.0当量)、6-甲基-2-乙烯基-1,3,6,2-二氧氮硼杂八环-4,8-二酮(2.63g,14.36mmol,1.2当量)和氯[(三叔丁基膦)-2-(2-氨基联苯基)]钯(II)(307mg,0.60mmol,0.05当量)装入装配有冷凝器、搅拌棒和氮气鼓泡器的250ml圆底烧瓶中。添加THF(100mL),接着针对氮气流添加N,N-二异丙基乙胺(4.2mL,23.94mmol,2.0当量)并将混合物加热至回流持续3h。
将粗产物通过快速柱色谱法进行纯化,以得到呈灰白色固体的2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(6-甲基-4,8-二氧代-1,3,6,2-二氧氮硼杂八环-2-基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(5.91g,11.4mmol,95%产率)。
1H NMR(400MHz,DMSO-d6)δ=7.63(dd,J=5.1,8.9Hz,1H),7.31(t,J=8.9Hz,1H),6.65(d,J=18.3Hz,1H),5.68(d,J=18.3Hz,1H),4.24(dd,J=11.9,17.2Hz,2H),3.95-3.83(m,2H),3.70(s,3H),2.66(spt,J=7.0Hz,1H),2.16(s,3H),0.90(d,J=7.0Hz,3H),0.89(d,J=7.0Hz,3H)
3.2 2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(3-甲基苯并三唑-5-基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(4.343)
将2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(6-甲基-4,8-二氧代-1,3,6,2-二氧氮硼杂八环-2-基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(700mg,1.35mmol)、1,1-双(二苯基膦基)二茂铁]二氯钯(II)二氯甲烷络合物[PdCl2(dppf).DCM](55mg,0.067mmol)、6-溴-1-甲基-苯并三唑(371mg,1.75mmol)和磷酸钾(1.17g,5.39mmol)添加到10-20ml微波小瓶中。添加2-甲基四氢呋喃(10ml)和水(0.5ml),然后通过抽空将反应混合物脱气并且回填氮气(X3)。在微波辐射下,将反应混合物加热至120℃持续60min。
将反应混合物通过塞过滤,用EtOAc和EtOH洗涤。将滤液在减压下浓缩以给出棕色胶状物(853mg)。将粗材料通过自动硅胶快速色谱法(用环己烷/乙酸乙酯梯度洗脱)纯化以给出呈橙色胶状物的2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(3-甲基苯并三唑-5-基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(4.343)(622mg,87%产率)
将经纯化的材料溶解于乙腈(10ml)并在室温下用SiliCycle硫醇(SH)金属清除剂树脂(622mg)进行处理。将悬浮液在室温下搅拌1.5h,然后过滤以除去树脂,用另外的乙腈洗涤。将滤液在真空中浓缩以提供呈白色固体的2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(3-甲基苯并三唑-5-基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(4.343)(583mg,87%产率)
1H NMR(400MHz,氯仿)7.96(d,J=9.0Hz,1H),7.39-7.49(m,3H),7.15(d,J=16.3Hz,1H),7.05(t,J=8.7Hz,1H),6.81(d,J=16.3Hz,1H),4.29(s,3H),3.68(s,3H),2.67(spt,J=7.0Hz,1H),2.23(s,3H),1.13(d,J=7.0Hz,3H),1.09(d,J=7.0Hz,3H)
3.3 2-甲基丙酸[5-[3-氯-6-氟-2-[2-(3-甲基苯并三唑-5-基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯
使2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(3-甲基苯并三唑-5-基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(496mg,1.00mmol)在3巴H2下在EtOAc(10mL)中在5%Pd/C(50%湿)催化剂(0.21g)上经受催化氢化持续18h。
将反应混合物通过垫过滤,用乙酸乙酯洗涤。将滤液在真空中浓缩以得到粗残余物(503mg),将其通过质量定向的反相HPLC纯化以得到呈无色胶状物的2-甲基丙酸[5-[3-氯-6-氟-2-[2-(3-甲基苯并三唑-5-基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(332mg,67%产率)
1H NMR(400MHz,氯仿)δ=7.92(d,J=8.6Hz,1H),7.43(dd,J=5.1,8.7Hz,1H),7.24(br s,1H),7.17(dd,J=1.3,8.6Hz,1H),7.01(t,J=8.7Hz,1H),4.26(s,3H),3.81(s,3H),3.11-2.91(m,3H),2.86-2.72(m,1H),2.54(spt,J=7.0Hz,1H),2.25(s,3H),0.98(d,J=7.1Hz,3H),0.96(d,J=7.0Hz,3H)
3.4 4-[3-氯-6-氟-2-[2-(3-甲基苯并三唑-5-基)乙基]苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(1.343)的制备
在室温下在乙醇(5ml)中搅拌2-甲基丙酸[5-[3-氯-6-氟-2-[2-(3-甲基苯并三唑-5-基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(332mg,0.67mmol)。逐滴地添加氢氧化锂一水合物(85mg,2.00mmol)在水中(2ml)的溶液,并将反应在室温下搅拌21h。
将乙醇溶剂在减压下除去,然后用水(20ml)稀释残余物。通过添加2M HCl(水性)将水相酸化至大约pH 3-4,然后将其用EtOAc(3×10ml)萃取。将合并的有机萃取物在减下压浓缩以给出白色固体(240mg)。将粗残余物通过自动硅胶快速色谱法(用环己烷/乙酸乙酯梯度洗脱)纯化以得到呈白色固体的4-[3-氯-6-氟-2-[2-(3-甲基苯并三唑-5-基)乙基]苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(1.343)(196mg,69%)
1H NMR(400MHz,乙腈)δppm 7.83(d,J=8.6Hz,1H),7.57(dd,J=5.2,8.8Hz,1H),7.33(s,1H),7.10-7.18(m,2H),4.22(s,3H),3.64(s,3H),2.84-3.07(m,4H)2.21(s,3H)
实例4 4-[2-[2-(1,3-苯并噻唑-5-基)乙基]-3-氯-6-氟-苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(1.350)的制备
4.1 4-[2-[(E)-2-(1,3-苯并噻唑-5-基)乙烯基]-3-氯-6-氟-苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮
将2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(6-甲基-4,8-二氧代-1,3,6,2-二氧氮硼杂八环-2-基)乙烯基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(500mg,0.96mmol)、5-溴-1,3-苯并噻唑(309mg,1.44mmol)、1,1-双(二苯基膦基)二茂铁]二氯钯(II)二氯甲烷络合物[PdCl2(dppf).DCM](4mg,0.05mmol)和碳酸钾(403mg,2.89mmol)在氮气气氛下添加到10-20ml微波小瓶中。添加经脱气的乙腈(8ml)和水(2ml)并将混合物在微波辐射下加热至150℃持续30min。
将反应混合物浓缩至干燥。将残余物用水(10ml)处理,并通过添加1M HCl(水性)将水相酸化至pH 4。添加DCM(20ml)并且分离层。将水相用DCM/MeOH(8:1)(2×10ml)进一步萃取,然后将合并的有机萃取物干燥并浓缩以给出棕色油状物。将粗材料通过自动硅胶快速色谱法(用环己烷/乙酸乙酯梯度洗脱)纯化以给出呈白色固体的4-[2-[(E)-2-(1,3-苯并噻唑-5-基)乙烯基]-3-氯-6-氟-苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(302mg,73%产率)。
将获得的产物溶解在甲醇/乙酸乙酯的3:2混合物(25ml)中。将溶液用活性炭(100mg)处理,然后在室温下搅拌1h。将混合物通过过滤,然后用额外的3:2MeOH/EtOAc(10ml)洗涤。将滤液用SiliCycle硫醇(SH)金属清除剂树脂(300mg)处理,然后在室温下搅拌16h。过滤混合物以除去树脂,然后将滤液在真空中浓缩以给出灰白色固体(286mg)。
1H NMR(400MHz,DMSO-d6)δ=10.84(br s,1H),9.41(s,1H),8.14(d,J=8.4Hz,1H),8.00(d,J=1.5Hz,1H),7.62(dd,J=5.1,8.7Hz,1H),7.54(dd,J=1.5,8.4Hz,1H),7.29(t,J=8.7Hz,1H),7.09(d,J=16.5Hz,1H),6.74(d,J=16.5Hz,1H),3.54(s,3H),2.18(s,3H)
4.2 4-[2-[2-(1,3-苯并噻唑-5-基)乙基]-3-氯-6-氟-苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(1.350)
向氮气氛下的4-[2-[(E)-2-(1,3-苯并噻唑-5-基)乙烯基]-3-氯-6-氟-苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(835mg,1.95mmol)在四氢呋喃(30ml)中的溶液中添加N,N-二异丙基乙胺(2.70ml,16.0mmol)。将搅拌的反应混合物加热至70℃并将2,4,6-三异丙基苯磺酰基酰肼(5.17g,15.6mmol)在4h内分批添加,然后将混合物加热至回流持续16h。将额外的N,N-二异丙基乙胺(1.70ml,9.80mmol)添加到反应混合物中,接着添加2,4,6-三异丙基苯磺酰基酰肼(3.24g,9.77mmol),并将混合物加热至回流持续另外的6h。
将反应混合物冷却至室温,然后直接浓缩到二氧化硅上。将粗材料通过自动硅胶快速色谱法(用环己烷/乙酸乙酯梯度洗脱)部分纯化。将所获得的材料通过质量定向的反相HPLC进一步纯化以得到呈淡黄色固体的4-[3-氯-6-氟-2-[2-[4-(甲基硫烷基甲基)苯基]乙基]苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(1.350)(227mg,27%产率)
1HNMR(500MHz,DMSO-d6)δppm10.84(br.s,1H),9.35(s,1H),8.03(d,J=8.3Hz,1H),7.71(d,J=1.0Hz,1H),7.55(dd,J=5.2,8.8Hz,1H),7.23(t,J=8.8Hz,1H),7.16(dd,J=1.0,8.3Hz,1H),3.62(s,3H),2.93-2.70(m,4H),2.26(s,3H)
实例5[3-氯-2-[2-(2,2-二甲基-1,3-苯并间二氧杂环戊烯-5-基)乙基]-6-氟-苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(1.361)的制备
5.1 2-甲基丙酸[5-[3-氯-6-氟-2-[2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯
将经烘箱干燥的圆底烧瓶然后装入Ir(COD)Cl2(299mg,0.45mmol)和4-二苯基磷烷基丁基(二苯基)磷烷(0380mg,0.89mmol)。将烧瓶排空并回填氮气(x 3),然后添加THF(75mL)并将反应在室温下搅拌30min。逐滴地添加2-甲基丙酸[5-(3-氯-6-氟-2-乙烯基-苯基)-1,3-二甲基-6-氧代-哒嗪-4-基]酯[如在实例4中所述的制备](6.7g,17.8mmol)在THF中的溶液并将混合物搅拌10min,接着逐滴地添加4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷(3.02mL,20.8mmol)。将反应在60℃下搅拌过夜。
24h后,将反应冷却至室温,然后在真空中浓缩。将粗产物通过硅胶柱色谱法(用环己烷/乙酸乙酯梯度洗脱)纯化以给出呈黄色固体的2-甲基丙酸[5-[3-氯-6-氟-2-[2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(4.50g,51%产率)。
1H NMR(500MHz,氯仿)δ=7.35(dd,J=5.2,8.9Hz,1H),6.90(t,J=8.6Hz,1H),3.81(s,3H),2.59(t,J=8.5Hz,2H),2.53(spt,J=7.0Hz,1H),2.24(s,3H),1.32-1.16(m,12H),1.08-1.00(m,2H),0.98(d,J=7.0Hz,3H),0.94(d,J=7.0Hz,3H)。
5.2[3-氯-2-[2-(2,2-二甲基-1,3-苯并间二氧杂环戊烯-5-基)乙基]-6-氟-苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(1.361)
将5-溴-2,2-二甲基-1,3-苯并间二氧杂环戊烯(70mg,0.30mmol)装入2-5ml的微波小瓶中。作为在1,4-二噁烷(2ml)中的溶液添加2-甲基丙酸[5-[3-氯-6-氟-2-[2-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)乙基]苯基]-1,3-二甲基-6-氧代-哒嗪-4-基]酯(100mg,0.20mmol),接着作为在1,4-二噁烷(2ml)中的溶液添加氯(2-二环己基膦基-2’,6’-二异丙氧基-1,1’-联苯基)[2-(2’-氨基-1,1’-联苯基)]钯(II)(RuPhos Pd-G2)(26mg,0.03mmol)。添加碳酸钾的2M水溶液(0.30ml,0.61mmol),并将混合物在微波辐射下加热至140℃持续80min。
将反应混合物冷却至室温,然后通过预先润湿的0.5g Silica-TMT柱过滤,用乙腈(2×2ml)洗涤。将滤液浓缩至干燥,然后通过质量定向的反相HPLC纯化以得到呈白色固体的[3-氯-2-[2-(2,2-二甲基-1,3-苯并间二氧杂环戊烯-5-基)乙基]-6-氟-苯基]-5-羟基-2,6-二甲基-哒嗪-3-酮(1.361)(15mg,17%产率)。
1H NMR(500MHz,氯仿)δppm7.43(dd,J=5.2,8.7Hz,1H),6.99(t,J=8.7Hz,1H),6.56(d,J=7.7Hz,1H),6.40-6.36(m,2H),3.74(s,3H),2.85-2.78(m,1H),2.77-2.61(m,3H),2.30(s,3H),1.65(s,3H),1.64(s,3H)
使用如上所述的通用方法制备化合物1.019、1.021、1.027、1.028、1.036、2.034、3.030、3.034、4.034、1.339、1.340、1.341、1.342、、1.344、1.345、1.346、1.347、1.348、1.349、1.351、1.352、1.353、1.354、1.355、1.356、1.044、1.053、1.357、1.358、1.359、1.360、2.362、2.363、和4.342。下表5示出了这些化合物的结构和NMR表征数据。
表5具有式(I)的化合物的制备实例。用于描述X和Y的位置的编号系统仅为清楚起见而示出。
生物学实例
B1出苗后功效-测试1
将以下多种测试物种的种子播种在盆中的标准土壤中:-龙葵(Solanum nigrum)(SOLNI)、反枝苋(Amaranthus retoflexus)(AMARE)、大狗尾草(Setaria faberi)(SETFA)、稗草(Echinochloa crus-galli)(ECHCG)、碗仔花(Ipomoea hederacea)(IPOHE)、多年生黑麦草(Lolium perenne)(LOLPE)。在温室中在受控条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下培养八天后(出苗后),用水性喷雾溶液喷洒这些植物,所述水性喷雾溶液源自工业级活性成分在丙酮/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 RN9005-64-5)。以250g/ha施用化合物。然后使测试植物在温室中在受控条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下生长,并且每日浇水两次。在13天之后,对所述测试给植物造成的损害百分比进行评价。以五分制评估生物活性(5=80%-100%;4=60%-79%;3=40%-59%;2=20%-39%;1=0-19%)。在表中的空白值表明那种化合物未在那种物种上进行测试。
表6出苗后施用后具有式(I)的化合物对杂草物种的控制
B2出苗后功效-测试2
将以下多种测试物种的种子播种在盆中的标准土壤中:-反枝苋(Amaranthusretoflexus)(AMARE)、大狗尾草(Setaria faberi)(SETFA)、稗草(Echinochloa crus-galli)(ECHCG)、碗仔花(Ipomoea hederacea)(IPOHE)、玉蜀黍(Zea Mays)(ZEAMX)、苘麻(Abutilon theophrasti)(ABUTH)。在温室中在受控条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下培养八天后(出苗后),用水性喷雾溶液喷洒这些植物,所述水性喷雾溶液源自工业级活性成分在丙酮/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)。以250g/ha施用化合物。然后使测试植物在温室中在受控条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下生长,并且每日浇水两次。在13天之后,对所述测试给植物造成的损害百分比进行评价。以五分制评估生物活性(5=80%-100%;4=60%-79%;3=40%-59%;2=20%-39%;1=0-19%)。在表中的空白值表明那种化合物未在那种物种上进行测试。
表7出苗后施用后具有式(I)的化合物对杂草物种的控制
B3出苗前功效-测试1
将以下多种测试物种的种子播种在盆中的标准土壤中:龙葵(Solanum nigrum)(SOLNI)、反枝苋(Amaranthus retoflexus)(AMARE)、大狗尾草(Setaria faberi)(SETFA)、稗草(Echinochloa crus-galli)(ECHCG)、碗仔花(Ipomoea hederacea)(IPOHE)、多年生黑麦草(Lolium perenne)(LOLPE)。在温室中在受控条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下培养一天之后(出苗前),用水性喷雾溶液喷洒这些植物,所述水性喷雾溶液源自工业级活性成分在丙酮/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 RN9005-64-5)。以250g/ha施用化合物。然后使测试植物在受控制的条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。在13天之后,对所述测试给植物造成的损害百分比进行评价。以五分制评估生物活性(5=80%-100%;4=60%-79%;3=40%-59%;2=20%-39%;1=0-19%)。在表中的空白值表明那种化合物未在那种物种上进行测试。
表8在出苗前施用之后具有式(I)的化合物对杂草物种的控制
B4出苗前功效-测试2
将以下多种测试物种的种子播种在盆中的标准土壤中:反枝苋(Amaranthusretoflexus)(AMARE)、大狗尾草(Setaria faberi)(SETFA)、稗草(Echinochloa crus-galli)(ECHCG)、碗仔花(Ipomoea hederacea)(IPOHE)、玉蜀黍(Zea Mays)(ZEAMX)、苘麻(Abutilon theophrasti)(ABUTH)。在温室中在受控条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下培养一天之后(出苗前),用水性喷雾溶液喷洒这些植物,所述水性喷雾溶液源自工业级活性成分在丙酮/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)。以250g/ha施用化合物。然后使测试植物在受控制的条件(在24℃/16℃白天/夜晚下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。在13天之后,对所述测试给植物造成的损害百分比进行评价。以五分制评估生物活性(5=80%-100%;4=60%-79%;3=40%-59%;2=20%-39%;1=0-19%)。在表中的空白值表明那种化合物未在那种物种上进行测试。
表9在出苗前施用之后具有式(I)的化合物对杂草物种的控制
Claims (20)
1.一种具有式(I)的化合物
或其盐或N-氧化物,其中,
R1选自由以下组成的组:C1-C4烷基、C3-C6环烷基、C3-C6烷氧基、C1-C2烷氧基-C1-C2烷基-、C2-C4烯基、C1-C4卤代烷基、氰基-C1-C4烷基、C2-C4卤代烯基、C2-C4炔基和C2-C4卤代炔基;
R2选自由以下组成的组:氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C3卤代烷氧基-C1-C3烷基-、C1-C6烷氧基、C1-C3烷氧基-C1-C3烷基、C1-C3烷氧基-C1-C3烷氧基-C1-C3烷基-、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C6羟基烷基-、C1-C6烷基羰基-、-S(O)mC1-C6烷基、氨基、C1-C6烷基氨基、C1-C6二烷基氨基、-C(C1-C3烷基)=N-O-C1-C3烷基和C2-C6卤代炔基;
G是氢、或C(O)R3;
R3选自由以下组成的组:C1-C6烷基、C2-C6烯基、C2-C6炔基、C1-C6烷基-S-、C1-C6烷氧基、-NR4R5和任选地被一个或多个R6取代的苯基;
R4和R5各自独立地选自由以下组成的组:氢、C1-C6烷基、C1-C6烷氧基和C3-C6环烷基,或者R4和R5一起可以形成吗啉基环;并且,
R6选自由以下组成的组:卤素、氰基、硝基、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基以及C1-C3卤代烷氧基;
X和Y各自独立地是氢、C1-C3烷基、环丙基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基、或卤素;
D是经取代或未经取代的萘环体系,或包含1、2、3或4个独立地选自氧、氮和硫的杂原子的经取代或未经取代的8-10元二环饱和、部分饱和或不饱和的杂环体系,并且其中当D被取代时,其在至少一个环碳原子上被R8取代和/或在至少一个环氮原子上被R9取代;
每个R8独立地是氧、羟基、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C3-C6-环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C3烷氧基-C1-C3烷基、C1-C3卤代烷氧基-C1-C3烷基-、C1-C3烷氧基-C1-C3烷氧基-C1-C3烷基-、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C1-C6羟基烷基-、C1-C6烷基羰基-、C1-C6卤代烷基羰基-、C3-C6环烷基羰基-、C1-C6烷基-S(O)m-、-S(O)m-C1-C6卤代烷基、-S(O)m-C3-C6环烷基、-O-S(O)2C1-C3烷基、-C1-C3烷基-S(O)m-C1-C6烷基、-C1-C3烷基-S(O)m-C1-C6卤代烷基、-C1-C3烷基-S(O)m-C3-C6环烷基、氰基-C1-C6-烷基-、-NR4R5、-C(C1-C3烷基)=N-O-C1-C3烷基、-C(S)NH2、C1-C6烷基氨基硫代羰基-、二(C1-C6烷基)氨基硫代羰基-、C3-C6-环烷基氨基-硫代羰基-S(O)2NH2、-S(O)2NHC(O)C1-C3烷基、C1-C6烷基氨基磺酰基-、二(C1-C6烷基)氨基磺酰基-、C3-C6-环烷基氨基-磺酰基-、-C(O)OH、-C(O)OC1-C6烷基、-C(O)NHS-(O)2C1-C6烷基、-C(O)NR4R5、-NR4C(O)NR4R5、C1-C6烷基羰基(C1-C6烷基)氨基-、C1-C6卤代烷基羰基氨基-、C1-C6卤代烷基羰基(C1-C6烷基)氨基-、C1-C6烷氧基羰基氨基-、C1-C6烷氧基羰基(C1-C6烷基)氨基-、C1-C6烷基磺酰基氨基-、C1-C6烷基磺酰基(C1-C6烷基)氨基-、C1-C6卤代烷基磺酰基氨基-、C1-C6卤代烷基磺酰基(C1-C6烷基)氨基-、C3-C6环烷基磺酰基氨基-、C3-C6环烷基磺酰基(C1-C6烷基)氨基-、C1-C6烷基氨基羰基氨基-、C1-C6烷基氨基羰基(C1-C6烷基)氨基、二(C1-C6烷基)氨基羰基氨基-、C1-C6卤代烷基氨基羰基氨基-、C1-C6卤代烷基氨基-羰基(C1-C6烷基)氨基、二(C1-C6卤代烷基)氨基羰基氨基-、二(C1-C6卤代烷基)氨基-羰基(C1-C6烷基)氨基-、羟基氨基-、羟基(C1-C6烷基)氨基、C1-C6烷氧基氨基、C1-C6烷氧基(C1-C6烷基)氨基、C1-C6卤代烷氧基氨基、C1-C6卤代烷氧基(C1-C6烷基)氨基、或选自由苯基环、5-6元杂芳基环和3-6元杂环基环组成的组的环体系,其中所述环体系被0至5个R16取代;
m是0、1或2的整数;
每个R9独立地是C1-C6烷基、C1-C6卤代烷基、羟基、C1-C4烷氧基、C1-C4烷硫基、C3-C6-环烷基、C1-C3烷氧基-C1-C3烷基、C1-C3卤代烷氧基-C1-C3烷基-、C1-C3烷氧基-C1-C3烷氧基-C1-C3烷基-、C1-C6羟基烷基-、-C1-C3烷基-S(O)m-C1-C6烷基、-C1-C3烷基-S(O)m-C1-C6卤代烷基、-C1-C3烷基-S(O)m-C3-C6环烷基、氰基-C1-C6-烷基-、或选自由苯基环、5-6元杂芳基环和3-6元杂环基环组成的组的环体系,其中所述环体系被0至5个R16取代;
每个R16独立地是卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基;并且,
W是
其中
“a”表示与苯基-哒嗪酮/苯基-哒嗪二酮部分的附接点,
“b”表示与环D的附接点,
R10、R12、R14和R15各自独立地是氢、C1-C3烷基或C1-C3卤代烷基;或者R10和R12与它们所连接的碳原子一起形成C3-C6碳环;并且
R11和R13各自独立地是氢、卤素、C1-C3烷基、或C1-C3卤代烷基,其前提是当R11或R13之一是卤素、C1-C3烷基或C1-C3卤代烷基时,另一个是氢。
2.根据权利要求1所述的化合物,其中,G是氢或C(O)R3,其中R3是异丙基、叔丁基、甲基、乙基、炔丙基、甲氧基、乙氧基、或叔丁氧基。
3.根据前述权利要求中任一项所述的化合物,其中,X是氢、卤素、或C1卤代烷基。
4.根据前述权利要求中任一项所述的化合物,其中,Y是氢、C1-C3烷基、环丙基、C1-C3卤代烷基、或卤素。
5.根据前述权利要求中任一项所述的化合物,其中,相对于所述哒嗪酮/哒嗪-二酮部分,X是在邻位。
6.根据前述权利要求中任一项所述的化合物,其中,相对于-W-D部分,Y是在邻位。
7.根据前述权利要求中任一项所述的化合物,其中,R1是甲基、乙基、正丙基、环丙基、炔丙基或C1卤代烷基。
8.根据前述权利要求中任一项所述的化合物,其中,R2选自由以下组成的组:氢、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C3烷氧基-C1-C3烷基、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基和C2-C6卤代炔基。
9.根据前述权利要求中任一项所述的化合物,其中,D是经取代或未经取代的萘、吲哚嗪、吲哚、异吲哚、吲哚啉、异吲哚啉、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并噁唑、苯并间二氧杂环戊烯、嘌呤、4H-喹嗪、喹啉、异喹啉、四氢喹啉、噌啉、酞嗪、喹喔啉、1-8-萘啶、蝶啶、1H-吡咯并[2,3-b]吡啶、咪唑并[1,2-a]吡嗪或1H-苯并三唑环体系,并且其中当D被取代时,其在至少一个环碳原子上被R8取代和/或在至少一个环氮原子上被R9取代。
10.根据前述权利要求中任一项所述的化合物,其中,D是经取代或未经取代的萘、吲哚嗪、吲哚、异吲哚、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并噁唑、嘌呤、4H-喹嗪、喹啉、异喹啉、四氢喹啉、噌啉、酞嗪、喹喔啉、1-8-萘啶、或蝶啶环体系,并且其中当D被取代时,其在至少一个环碳原子上被R8取代和/或在至少一个环氮原子上被R9取代。
11.根据前述权利要求中任一项所述的化合物,其中,每个R8独立地是氧、羟基、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C3卤代烷氧基-C1-C3烷基-、C1-C6烷氧基、C1-C3烷氧基-C1-C3烷基、C1-C3烷氧基-C1-C3烷氧基-C1-C3烷基-、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C6羟基烷基-、C1-C6烷基羰基-、C1-C6烷基-S(O)m-、氨基、C1-C6烷基氨基、C1-C6二烷基氨基、-C(C1-C3烷基)=N-O-C1-C3烷基或C2-C6卤代炔基。
12.根据前述权利要求中任一项所述的化合物,其中,每个R9独立地是C1-C4烷基、C1-C4卤代烷基、羟基、C1-C4烷氧基、或C1-C4烷硫基。
13.根据前述权利要求中任一项所述的化合物,其中,W是W1并且R10、R11、R12和R13各自是氢。
14.根据权利要求1至12中任一项所述的化合物,其中,W是W2并且R14和R15各自是氢。
16.一种除草组合物,其包含根据权利要求1-15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。
17.根据权利要求16所述的除草组合物,其进一步包含至少一种额外的杀有害生物剂。
18.根据权利要求17所述的除草组合物,其中,所述额外的杀有害生物剂是除草剂或除草剂安全剂。
19.一种控制不想要的植物生长的方法,所述方法包括将如权利要求1至15中任一项所定义的具有式(I)的化合物或根据权利要求16至18中任一项所述的除草组合物施用至不想要的植物或其场所。
20.如权利要求1至15中任一项所定义的具有式(I)的化合物作为除草剂的用途。
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PCT/EP2020/070243 WO2021009335A1 (en) | 2019-07-18 | 2020-07-17 | Substituted pyridazinones as herbicides |
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BR112023022201A2 (pt) | 2021-04-27 | 2023-12-26 | Bayer Ag | Piridazinonas substituídas, sais ou n-óxidos dos mesmos e seus usos como substâncias herbicidamente ativas |
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AU2020313369A1 (en) | 2022-01-27 |
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US20220281837A1 (en) | 2022-09-08 |
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WO2021009335A1 (en) | 2021-01-21 |
TW202116737A (zh) | 2021-05-01 |
UY38788A (es) | 2021-02-26 |
KR20220035372A (ko) | 2022-03-22 |
AR119411A1 (es) | 2021-12-15 |
JP2022540908A (ja) | 2022-09-20 |
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