CN113329629A - 除草化合物 - Google Patents
除草化合物 Download PDFInfo
- Publication number
- CN113329629A CN113329629A CN201980074495.3A CN201980074495A CN113329629A CN 113329629 A CN113329629 A CN 113329629A CN 201980074495 A CN201980074495 A CN 201980074495A CN 113329629 A CN113329629 A CN 113329629A
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- CN
- China
- Prior art keywords
- alkyl
- group
- radical
- formula
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 197
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 18
- 239000004009 herbicide Substances 0.000 claims abstract description 15
- -1 C2-C6Alkenyl radical Chemical class 0.000 claims description 206
- 239000001257 hydrogen Substances 0.000 claims description 141
- 229910052739 hydrogen Inorganic materials 0.000 claims description 141
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 125
- 150000003254 radicals Chemical class 0.000 claims description 123
- 125000000623 heterocyclic group Chemical group 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 84
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 78
- 150000002431 hydrogen Chemical class 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- 125000005842 heteroatom Chemical group 0.000 claims description 52
- 238000006467 substitution reaction Methods 0.000 claims description 45
- 229910052717 sulfur Inorganic materials 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 28
- 229910004749 OS(O)2 Inorganic materials 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 8
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- 125000005466 alkylenyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- 239000012872 agrochemical composition Substances 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 32
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 13
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004007 reversed phase HPLC Methods 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002671 adjuvant Substances 0.000 description 10
- 150000001721 carbon Chemical group 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000002168 alkylating agent Substances 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000000575 pesticide Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 244000038559 crop plants Species 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 235000013311 vegetables Nutrition 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 239000005582 Metosulam Substances 0.000 description 5
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- CTOFEQTWXKUYSM-UHFFFAOYSA-M methyl 3-[4-[methyl(phenyl)carbamoyl]pyridazin-1-ium-1-yl]propanoate bromide Chemical compound [Br-].CN(C(=O)C1=CN=[N+](C=C1)CCC(=O)OC)C1=CC=CC=C1 CTOFEQTWXKUYSM-UHFFFAOYSA-M 0.000 description 5
- 239000003094 microcapsule Substances 0.000 description 5
- 125000002757 morpholinyl group Chemical group 0.000 description 5
- 125000003386 piperidinyl group Chemical group 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- JUSIWJONLKBPDU-UHFFFAOYSA-N pyridazine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NN=C1 JUSIWJONLKBPDU-UHFFFAOYSA-N 0.000 description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
- 240000006122 Chenopodium album Species 0.000 description 4
- 235000009344 Chenopodium album Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- IENWQEHCKGQRQI-UHFFFAOYSA-N N-methylpyridazine-4-carboxamide Chemical compound CNC(=O)c1ccnnc1 IENWQEHCKGQRQI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 4
- 238000010353 genetic engineering Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000004892 pyridazines Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical group CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 3
- 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 3
- MDBYQCZJOFFBID-UHFFFAOYSA-N 2-(5,5-dimethyl-4H-1,2-oxazol-3-yl)ethylazanium 2,2,2-trifluoroacetate Chemical compound FC(C(=O)[O-])(F)F.CC1(CC(=NO1)CC[NH3+])C MDBYQCZJOFFBID-UHFFFAOYSA-N 0.000 description 3
- KKIKBMZTACZXGC-UHFFFAOYSA-N 2-[4-(methylcarbamoyl)pyridazin-1-ium-1-yl]ethanesulfonate Chemical compound CNC(=O)C1=CN=[N+](C=C1)CCS(=O)(=O)[O-] KKIKBMZTACZXGC-UHFFFAOYSA-N 0.000 description 3
- UIRQZLWYWIUFSC-UHFFFAOYSA-N 2-pyridazin-4-yl-1,3-benzoxazole Chemical class N1=NC=C(C=C1)C=1OC2=C(N=1)C=CC=C2 UIRQZLWYWIUFSC-UHFFFAOYSA-N 0.000 description 3
- MXYJAVLADSCZLZ-UHFFFAOYSA-N 3-[4-(piperidine-1-carbonyl)pyridazin-1-ium-1-yl]propanoic acid 2,2,2-trifluoroacetate Chemical compound C1CCN(CC1)C(=O)C2=CN=[N+](C=C2)CCC(=O)O.C(=O)(C(F)(F)F)[O-] MXYJAVLADSCZLZ-UHFFFAOYSA-N 0.000 description 3
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- GTXLEKJDRPBWQL-UHFFFAOYSA-N CC1(C)ON=C(CCNC(C2=CN=[N+](CCC([O-])=O)C=C2)=O)C1 Chemical compound CC1(C)ON=C(CCNC(C2=CN=[N+](CCC([O-])=O)C=C2)=O)C1 GTXLEKJDRPBWQL-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- 244000025670 Eleusine indica Species 0.000 description 3
- 235000014716 Eleusine indica Nutrition 0.000 description 3
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 3
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 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 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- KDXMKAHKGZBUFC-UHFFFAOYSA-N N,3-dimethylpyridazine-4-carboxamide Chemical compound CNC(=O)c1ccnnc1C KDXMKAHKGZBUFC-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- QPHCFTQLFZVTMW-UHFFFAOYSA-N N-[2-(5,5-dimethyl-4H-1,2-oxazol-3-yl)ethyl]pyridazine-4-carboxamide Chemical compound CC1(CC(=NO1)CCNC(=O)C1=CN=NC=C1)C QPHCFTQLFZVTMW-UHFFFAOYSA-N 0.000 description 3
- OBIPOUXDDHTDPL-UHFFFAOYSA-N N-methyl-N-phenylpyridazine-4-carboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC=NN=C1 OBIPOUXDDHTDPL-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- XOGCTUKDUDAZKA-UHFFFAOYSA-N tetrapropylphosphanium Chemical compound CCC[P+](CCC)(CCC)CCC XOGCTUKDUDAZKA-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical compound C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- OOLZXLYYPCOPQZ-UHFFFAOYSA-N tripropylsulfanium Chemical compound CCC[S+](CCC)CCC OOLZXLYYPCOPQZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003954 δ-lactams Chemical class 0.000 description 1
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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
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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Abstract
具有式(I)的化合物用作除草剂的用途,其中取代基是如本文所定义的。还要求保护具有式(I)的化合物。
Description
本发明涉及除草活性的哒嗪衍生物,并且涉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,并且延伸到此类化合物和组合物在有用植物的作物中用于控制不希望的植物生长的用途:特别是用于控制杂草的用途。
天然产物哒酮霉素(pyridazomycin)是哒嗪衍生物的一个实例,并且首次作为新的抗真菌抗生素披露于The Journal Of Antibiotics[抗生素杂志],1988,41(5),595-601中。已经披露了哒酮霉素的另外的哒嗪衍生物并且测试了其抗微生物活性,参见Arch.Pharm.1995,328(4),307-312和Pharmazie 1996,51(2),76-83。
本发明是基于以下发现,即:具有如本文定义的式(I)的哒嗪衍生物
表现出意外良好的除草活性。因此,根据本发明,提供了具有式(I)的化合物或其农艺学上可接受的盐或两性离子物种作为除草剂的用途:
其中
R1选自由以下各项组成的组:氢、卤素、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、-OR7、-OR15a、-N(R6)S(O)2R15、-N(R6)C(O)R15、-N(R6)C(O)OR15、–N(R6)C(O)NR16R17、-N(R6)CHO、-N(R7a)2和-S(O)rR15;
R2选自由以下各项组成的组:氢、卤素、C1-C6烷基和C1-C6卤代烷基;
并且其中当R1选自由–OR7、-OR15a、-N(R6)S(O)2R15、-N(R6)C(O)R15、-N(R6)C(O)OR15、–N(R6)C(O)NR16R17、-N(R6)CHO、-N(R7a)2和-S(O)rR15组成的组时,R2选自由氢和C1-C6烷基组成的组;或者
R1和R2与它们所附接的碳原子一起形成C3-C6环烷基环或3元至6元杂环基,该杂环基包含1或2个单独地选自N和O的杂原子;并且
Q是(CR1aR2b)m;
m是0、1、2或3;
每个R1a和R2b独立地选自由以下各项组成的组:氢、卤素、C1-C6烷基、C1-C6卤代烷基、-OH、-OR7、-OR15a、-NH2、-NHR7、-NHR15a、-N(R6)CHO、-NR7bR7c以及–S(O)rR15;或者
每个R1a和R2b与它们所附接的碳原子一起形成C3-C6环烷基环或3元至6元杂环基,该杂环基包含1或2个单独地选自N和O的杂原子;并且
R3、R4和R5独立地选自由以下各项组成的组:氢、氰基、硝基、C1-C6烷基、C1-C6硫代烷基、C1-C6氟烷基、C1-C6氟烷氧基、C1-C6烷氧基、C3-C6环烷基、苯基和-N(R6)2;
每个R6独立地选自氢和C1-C6烷基;
每个R7独立地选自由以下各项组成的组:C1-C6烷基、-S(O)2R15、-C(O)R15、-C(O)OR15以及-C(O)NR16R17;
每个R7a独立地选自由以下各项组成的组:-S(O)2R15、-C(O)R15、-C(O)OR15、-C(O)NR16R17和-C(O)NR6R15a;
R7b和R7c独立地选自由以下各项组成的组:C1-C6烷基、-S(O)2R15、-C(O)R15、-C(O)OR15、-C(O)NR16R17和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;或者
R7b和R7c与它们所附接的氮原子一起形成4元至6元杂环基环,该杂环基环任选地包含一个另外的单独地选自N、O和S的杂原子;并且
R8a选自由以下各项组成的组:氢、-OH、-OR7、-S(O)rR15、-C(O)OR10、-C(O)R15、-C(O)NR16R17、-S(O)2NR16R17、-NR7dR7e、R15S(O)rC1-C3烷基-、R16R17NS(O)2C1-C3烷基-、R15C(O)C1-C3烷基-、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷氧基、C3-C6环烷基C1-C3烷基-、C3-C6环烷基C1-C3烷氧基-、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、C1-C3烷氧基C1-C3烷氧基-、C1-C6卤代烷氧基、C1-C3卤代烷氧基C1-C3烷基-、C3-C6烯基氧基、C3-C6炔基氧基、-C(R6)=NOR6、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1、2或3个可以是相同或不同的R9取代基取代;
R8b选自由以下各项组成的组:氢、-OR7、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷氧基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、C1-C3烷氧基C1-C3烷氧基-、C1-C6卤代烷氧基、C1-C3卤代烷氧基C1-C3烷基-、C3-C6烯基氧基以及C3-C6炔基氧基;或者
R8a和R8b与它们所附接的氮原子一起形成4元至6元杂环基,其任选地包含1或2个另外的独立地选自N、O和S(O)r的杂原子,并且其中所述杂环基部分任选地被1或2个可以是相同或不同的R9取代基取代;并且
R7d和R7e独立地选自由以下各项组成的组:氢、C1-C6烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C1-C3烷氧基C1-C3烷基-、C2-C6炔基、-S(O)2R15、-C(O)R15、-C(O)OR15、-C(O)NR16R17和苯基,并且其中所述苯基任选地被1、2或3个R9取代基取代;
每个R9独立地选自由以下各项组成的组:-OH、卤素、氰基、-N(R6)2、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基;
X选自由以下各项组成的组:C3-C6环烷基、苯基、包含1、2、3或4个单独地选自N、O和S的杂原子的5元或6元杂芳基、和包含1、2或3个单独地选自N、O和S的杂原子的4元至6元杂环基,并且其中所述环烷基、苯基、杂芳基或杂环基部分任选地被1或2个R9取代基取代,并且其中前述CR1R2、Q和Z部分可以附接在所述环烷基、苯基、杂芳基或杂环基部分的任何位置;
n是0或1;
Z选自由以下各项组成的组:-C(O)OR10、-CH2OH、-CHO、-C(O)NHOR11、-C(O)NHCN、-OC(O)NHOR11、-OC(O)NHCN、-NR6C(O)NHOR11、-NR6C(O)NHCN、-C(O)NHS(O)2R12、-OC(O)NHS(O)2R12、-NR6C(O)NHS(O)2R12、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10、-NR6S(O)OR10、-NHS(O)2R14、-S(O)OR10、-OS(O)OR10、-S(O)2NHCN、-S(O)2NHC(O)R18、-S(O)2NHS(O)2R12、-OS(O)2NHCN、-OS(O)2NHS(O)2R12、-OS(O)2NHC(O)R18、-NR6S(O)2NHCN、-NR6S(O)2NHC(O)R18、-N(OH)C(O)R15、-ONHC(O)R15、-NR6S(O)2NHS(O)2R12、-P(O)(R13)(OR10)、-P(O)H(OR10)、-OP(O)(R13)(OR10)、-NR6P(O)(R13)(OR10)和四唑;
R10选自由以下各项组成的组:氢、C1-C6烷基、苯基和苄基,并且其中所述苯基或苄基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R11选自由以下各项组成的组:氢、C1-C6烷基和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R12选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、-OH、-N(R6)2和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R13选自由以下各项组成的组:-OH、C1-C6烷基、C1-C6烷氧基和苯基;
R14是C1-C6卤代烷基;
R15选自由以下各项组成的组:C1-C6烷基和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R15a是苯基,其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R16和R17独立地选自由以下各项组成的组:氢和C1-C6烷基;或者
R16和R17与它们所附接的氮原子一起形成4元至6元杂环基环,其任选地包含一个另外的独立地选自N、O和S的杂原子;并且
R18选自由以下各项组成的组:氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、-N(R6)2和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
并且
r是0、1或2。
某些具有式(I)的化合物是已知的:
i)化合物:
5-(4-氨基甲酰基哒嗪-1-鎓-1-基)戊酸
或
ii)化合物:
2-氨基-4-(4-氨基甲酰基哒嗪-1-鎓-1-基)丁酸
或
iii)化合物:
2-氨基-5-(4-氨基甲酰基哒嗪-1-鎓-1-基)戊酸。
因此,在本发明第二方面中,提供了不是以上列出的i)(5-(4-氨基甲酰基哒嗪-1-鎓-1-基)戊酸)、ii)(2-氨基-4-(4-氨基甲酰基哒嗪-1-鎓-1-基)丁酸)或iii)(2-氨基-5-(4-氨基甲酰基哒嗪-1-鎓-1-基)戊酸)的具有式(I)的化合物。
根据本发明的第三方面,提供了一种农用化学组合物,其包含除草有效量的具有式(I)的化合物和农用化学上可接受的稀释剂或载体。这种农业组合物可以进一步包含至少一种另外的活性成分。
根据本发明的第四方面,提供了一种用于控制或防止不希望的植物生长的方法,其中将除草有效量的具有式(I)的化合物或包含这种化合物作为活性成分的组合物施用至这些植物、其部分或其场所。
如本文使用的,术语“卤素(halogen或halo)”是指氟(fluorine,fluoro)、氯(chlorine,chloro)、溴(bromine,bromo)或碘(iodine,iodo),优选氟、氯或溴。
如本文使用的,氰基意指-CN基团。
如本文使用的,羟基意指-OH基团。
如本文使用的,硝基意指-NO2基团。
如本文使用的,术语“C1-C6烷基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,其不含不饱和度,具有从一至六个碳原子,并且通过单键附接至分子的剩余部分。C1-C4烷基和C1-C2烷基应相应地解释。C1-C6烷基的实例包括但不限于甲基(Me)、乙基(Et)、正丙基、1-甲基乙基(异丙基)、正丁基和1-二甲基乙基(叔丁基或tBu)。
如本文使用的,术语“C1-C6烷氧基”是指具有式-ORa的基团,其中Ra是如上一般定义的C1-C6烷基。C1-C4烷氧基应相应地解释。C1-4烷氧基的实例包括但不限于甲氧基、乙氧基、丙氧基、异丙氧基和叔丁氧基。
如本文使用的,术语“C1-C6卤代烷基”是指如上一般定义的C1-C6烷基基团,其被一个或多个相同或不同的卤素原子取代。C1-C4卤代烷基应相应地解释。C1-C6卤代烷基的实例包括但不限于氯甲基、氟甲基、氟乙基、二氟甲基、三氟甲基和2,2,2-三氟乙基。
如本文使用的,术语“C2-C6烯基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,其含有至少一个可以具有(E)-或(Z)-构型的双键,具有从二至六个碳原子,通过单键附接至分子的剩余部分。C2-C4烯基应相应地解释。C2-C6烯基的实例包括但不限于丙-1-烯基、烯丙基(丙-2-烯基)和丁-1-烯基。
如本文使用的,术语“C2-C6卤代烯基”是指如上一般定义的C2-C6烯基基团,其被一个或多个相同或不同的卤素原子取代。C2-C6卤代烯基的实例包括但不限于氯乙烯、氟乙烯、1,1-二氟乙烯、1,1-二氯乙烯和1,1,2-三氯乙烯。
如本文使用的,术语“C2-C6炔基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,其包含至少一个三键,具有从二至六个碳原子,并且通过单键附接至分子的剩余部分。C2-C4炔基应相应地解释。C2-C6炔基的实例包括但不限于丙-1-炔基、炔丙基(丙-2-炔基)和丁-1-炔基。
如本文使用的,术语“C1-C6卤代烷氧基”是指如上定义的C1-C6烷氧基基团,其被一个或多个相同或不同的卤素原子取代。C1-C4卤代烷氧基应相应地解释。C1-C6卤代烷氧基的实例包括但不限于氟甲氧基、二氟甲氧基、氟乙氧基、三氟甲氧基和三氟乙氧基。
如本文使用的,术语“C1-C3卤代烷氧基C1-C3烷基”是指具有式Rb-O-Ra-的基团,其中Rb是如上一般定义的C1-C3卤代烷基基团,并且Ra是如上一般定义的C1-C3亚烷基基团。
如本文使用的,术语“C1-C3烷氧基C1-C3烷基”是指具有式Rb-O-Ra-的基团,其中Rb是如上一般定义的C1-C3烷基基团,并且Ra是如上一般定义的C1-C3亚烷基基团。
如本文使用的,术语“C1-C3烷氧基C1-C3烷氧基”是指具有式Rb-O-Ra-O-的基团,其中Rb是如上一般定义的C1-C3烷基基团,并且Ra是如上一般定义的C1-C3亚烷基基团。
如本文使用的,术语“C3-C6烯基氧基”是指具有式-ORa的基团,其中Ra是如上一般定义的C3-C6烯基基团。
如本文使用的,术语“C3-C6炔基氧基”是指具有式-ORa的基团,其中Ra是如上一般定义的C3-C6炔基基团。
如本文使用的,术语“羟基C1-C6烷基”是指被一个或多个羟基基团取代的如上一般定义的C1-C6烷基基团。
如本文使用的,术语“氰基C1-C6烷基”是指如上一般定义的C1-C6烷基基团,其被一个或多个氰基基团取代。
如本文使用的,术语“C3-C6环烷基”是指稳定的单环基团,其是饱和的或部分不饱和的并且含有3至6个碳原子。C3-C4环烷基应相应地解释。C3-C6环烷基的实例包括但不限于环丙基、环丁基、环戊基和环己基。
如本文使用的,术语“C3-C6卤代环烷基”是指被一个或多个相同的或不同的卤素原子取代的如上一般定义的C3-C6环烷基基团。C3-C4卤代环烷基应相应地解释。
如本文使用的,术语“C3-C6环烷氧基”是指具有式-ORa的基团,其中Ra是如上一般定义的C3-C6环烷基基团。
如本文使用的,术语“C3-C6环烷基C1-C3烷基”是指通过如上定义的C1-C3亚烷基基团附接至分子的剩余部分的如上定义的C3-C6环烷基环。C3-C6环烷基C1-C3烷基-的实例包括但不限于环丙基-甲基-和环丁基-乙基-。
如本文使用的,术语“C3-C6环烷基C1-C3烷氧基-”是指通过如上定义的C1-C3烷氧基基团附接至分子的剩余部分的如上定义的C3-C6环烷基环。C3-C6环烷基C1-C3烷氧基-的实例包括但不限于环丙基甲氧基-。
如本文使用的,除非另外明确说明,术语“杂芳基”是指包含1、2、3或4个单独地选自氮、氧和硫的杂原子的5元或6元单环芳香族环。该杂芳基基团可以经由碳原子或杂原子键合至分子的剩余部分。杂芳基的实例包括呋喃基、吡咯基、咪唑基、噻吩基、吡唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、三唑基、四唑基、吡嗪基、哒嗪基、嘧啶基或吡啶基。
如本文使用的,除非另外明确说明,术语“杂环基”或“杂环的”是指包含1、2或3个单独地选自氮、氧和硫的杂原子的稳定的3元至6元非芳香族单环基团。该杂环基基团可以经由碳原子或杂原子键合至分子的剩余部分。杂环基的实例包括但不限于吡咯啉基、吡咯烷基、四氢呋喃基、四氢噻吩基、四氢噻喃基、哌啶基、哌嗪基、四氢吡喃基、二氢异噁唑基、二氧戊环基、吗啉基或δ-内酰胺基(δ-lactamyl)。
如本文使用的,术语“杂环基C1-C2烷基-”是指通过如上定义的C1-C2亚烷基基团附接至分子的剩余部分的如上定义的杂环基环。
如本文使用的,术语“杂芳基C1-C2烷基-”是指通过如上定义的C1-C2亚烷基基团附接至分子的剩余部分的如上定义的杂芳基环。
如本文使用的,术语“苯基C1-C2烷基-”是指通过如如上定义的C1-C2亚烷基基团附接至分子的剩余部分的苯环。苯基C1-C2烷基-的实例包括但不限于苄基。
在具有式(I)的化合物中一个或多个可能的不对称碳原子的存在意味着所述化合物能以手性异构体形式存在,即对映异构体或非对映异构体的形式。作为围绕单键的受限旋转的结果,还可能存在阻转异构体。式(I)旨在包括所有那些可能的异构体形式及其混合物。本发明包括具有式(I)的化合物的所有那些可能的异构体形式及其混合物。同样地,式(I)旨在包括所有可能的互变异构体(包括内酰胺-内酰亚胺互变异构和酮-烯醇互变异构)(当存在时)。本发明包括具有式(I)的化合物的所有可能的互变异构体形式。类似地,在存在双取代烯烃的情况下,这些能以E或Z形式或作为呈任何比例的二者的混合物存在。本发明包括具有式(I)的化合物的所有这些可能的异构体形式及其混合物。
具有式(I)的化合物将典型地以农艺学上可接受的盐、两性离子或农艺学上可接受的两性离子盐的形式提供。本发明涵盖所有此类农艺学上可接受的盐、两性离子及其呈所有比例的混合物。
例如,具有式(I)的化合物(其中Z包含酸性质子)可以作为以下存在:两性离子,即具有式(I-I)的化合物,或农艺学上可接受的盐,即具有式(I-II)的化合物,如下所示:
其中,Y表示农艺学上可接受的阴离子,并且j和k表示可选自1、2或3的整数,取决于相应阴离子Y的电荷。
具有式(I)的化合物也可以作为农艺学上可接受的两性离子盐存在,即具有式(I-III)的化合物,如下所示:
其中,Y表示农艺学上可接受的阴离子,M表示农艺学上可接受的阳离子(除哒嗪鎓阳离子外),并且整数j、k和q可以选自1、2或3,取决于相应阴离子Y和相应阳离子M的电荷。
因此,当本文中以质子化形式绘制具有式(I)的化合物时,技术人员将理解,它同样可以以未质子化或盐形式(具有一种或多种相关抗衡离子)表示。技术人员还将认识到,R1、R2、Q或X中包含的氮原子也可以被质子化(例如参见表A中的化合物A12)。
本发明的合适的农艺学上可接受的盐(由阴离子Y表示)包括但不限于氯化物、溴化物、碘化物、氟化物、2-萘磺酸盐、乙酸盐、己二酸盐、甲醇盐、乙醇盐、丙醇盐、丁醇盐、天冬氨酸盐、苯磺酸盐、苯甲酸盐、碳酸氢盐、硫酸氢盐、酒石酸氢盐、丁基硫酸盐、丁基磺酸盐、丁酸盐、樟脑酸盐、樟脑磺酸盐(camsylate)、癸酸盐、己酸盐、辛酸盐、碳酸盐、柠檬酸盐、二磷酸盐、依地酸盐、乙二磺酸盐、庚酸盐、乙二磺酸盐、乙磺酸盐、乙基硫酸盐、甲酸盐、富马酸盐、葡庚糖酸盐、葡糖酸盐、葡糖醛酸盐、谷氨酸盐、甘油磷酸盐、十七烷酸盐、十六烷酸盐、硫酸氢盐、氢氧化物、羟萘甲酸盐、羟乙磺酸盐、乳酸盐、乳糖醛酸盐、月桂酸盐、苹果酸盐、马来酸盐、扁桃酸盐、甲磺酸盐、甲二磺酸盐、甲基硫酸盐、粘酸盐、肉豆蔻酸盐、萘磺酸盐、硝酸盐、十九烷酸盐、十八烷酸盐、草酸盐、壬酸盐、十五烷酸盐、五氟丙酸盐、高氯酸盐、磷酸盐、丙酸盐、丙基硫酸盐、丙磺酸盐、琥珀酸盐、硫酸盐、酒石酸盐、甲苯磺酸盐、十三烷酸盐(tridecylate)、三氟甲磺酸盐、三氟乙酸盐、十一烷酸盐(undecylinate)和戊酸盐。
由M表示的合适的阳离子包括但不限于金属、胺的共轭酸和有机阳离子。合适的金属的实例包括铝、钙、铯、铜、锂、镁、锰、钾、钠、铁和锌。合适的胺的实例包括烯丙胺、氨、戊胺、精氨酸、苯乙苄胺、苄星青霉素、丁烯基-2-胺、丁胺、丁基乙醇胺、环己胺、癸胺、二戊胺、二丁胺、二乙醇胺、二乙胺、二乙三胺、二庚胺、二己胺、二异戊胺、二异丙胺、二甲胺、二辛胺、二丙醇胺、二炔丙胺、二丙胺、十二胺、乙醇胺、乙胺、乙基丁胺、乙二胺、乙基庚胺、乙基辛胺、乙基丙醇胺、十七胺、庚胺、十六胺、己烯基-2-胺、己胺、己基庚胺、己基辛胺、组氨酸、吲哚啉、异戊胺、异丁醇胺、异丁胺、异丙醇胺、异丙胺、赖氨酸、葡甲胺、甲氧基乙胺、甲胺、甲基丁胺、甲基乙胺、甲基己胺、甲基异丙胺、甲基壬胺、甲基十八胺、甲基十五胺、吗啉、N,N-二乙基乙醇胺、N-甲基哌嗪、壬胺、十八胺、辛胺、油胺、十五胺、戊烯基-2-胺、苯氧基乙胺、甲基吡啶、哌嗪、哌啶、丙醇胺、丙胺、丙二胺、吡啶、吡咯烷、仲丁胺、硬脂酰胺、牛脂胺、十四胺、三丁胺、三癸胺、三甲胺、三庚胺、三己胺、三异丁胺、三异癸胺、三异丙胺、三甲胺、三戊胺、三丙胺、三(羟甲基)氨基甲烷和十一胺。合适的有机阳离子的实例包括苄基三丁基铵、苄基三甲基铵、苄基三苯基鏻、胆碱、四丁基铵、四丁基鏻、四乙基铵、四乙基鏻、四甲基铵、四甲基鏻、四丙基铵、四丙基鏻、三丁基锍、三丁基氧化锍、三乙基锍、三乙基氧化锍、三甲基锍、三甲基氧化锍、三丙基锍和三丙基氧化锍。
优选的其中Z包含酸性质子的具有式(I)的化合物可以表示为(I-I)或(I-II)。对于具有式(I-II)的化合物,重点是当Y是氯离子、溴离子、碘离子、氢氧根、碳酸氢根、乙酸根、五氟丙酸根、三氟甲磺酸根、三氟乙酸根、硫酸氢根、甲基硫酸根、甲苯磺酸根和硝酸根时的盐,其中j和k是1。优选地,Y是氯离子、溴离子、碘离子、氢氧根、碳酸氢根、乙酸根、三氟乙酸根、甲基硫酸根、甲苯磺酸根和硝酸根,其中j和k是1。对于具有式(I-II)的化合物,重点还是当Y是碳酸根和硫酸根(其中j为2且k为1)时以及当Y是磷酸根(其中j为3且k为1)时的盐。
适当时,具有式(I)的化合物也可以处于N-氧化物的形式(和/或用作N-氧化物)。
其中m为0且n为0的具有式(I)的化合物可以由具有式(I-Ia)的化合物表示,如下所示:
其中R1、R2、R3、R4、R5、R8a、R8b和Z是如针对具有式(I)的化合物所定义的。
其中m为1且n为0的具有式(I)的化合物可以由具有式(I-Ib)的化合物表示,如下所示:
其中R1、R2、R1a、R2b、R3、R4、R5、R8a、R8b和Z是如针对具有式(I)的化合物所定义的。
其中m为2且n为0的具有式(I)的化合物可以由具有式(I-Ic)的化合物表示,如下所示:
其中R1、R2、R1a、R2b、R3、R4、R5、R8a、R8b和Z是如针对具有式(I)的化合物所定义的。
其中m为3且n为0的具有式(I)的化合物可以由具有式(I-Id)的化合物表示,如下所示:
其中R1、R2、R1a、R2b、R3、R4、R5、R8a、R8b和Z是如针对具有式(I)的化合物所定义的。
以下列表提供了关于根据本发明的具有式(I)的化合物的取代基n、m、r、Q、X、Z、R1、R2、R1a、R2b、R2、R3、R4、R5、R6、R7、R7a、R7b、R7c、R7d、R7e、R8a、R8b、R9、R10、R11、R12、R13、R14、R15、R15a、R16、R17和R18的定义,包括优选定义。对于这些取代基中的任何一个,以下给出的任何定义都可以结合以下或在本文件中的其他地方给出的任何其他取代基的任何定义。
R1选自由以下各项组成的组:氢、卤素、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、-OR7、-OR15a、-N(R6)S(O)2R15、-N(R6)C(O)R15、-N(R6)C(O)OR15、-N(R6)C(O)NR16R17、-N(R6)CHO、-N(R7a)2和-S(O)rR15。优选地,R1选自由以下各项组成的组:氢、卤素、C1-C6烷基、C1-C6氟烷基、-OR7、-NHS(O)2R15、-NHC(O)R15、-NHC(O)OR15、-NHC(O)NR16R17、-N(R7a)2和-S(O)rR15。更优选地,R1选自由以下各项组成的组:氢、卤素、C1-C6烷基、C1-C6氟烷基、-OR7和-N(R7a)2。甚至更优选地,R1选自由以下各项组成的组:氢、C1-C6烷基、-OR7和-N(R7a)2。甚至还更优选地,R1是氢或C1-C6烷基。又甚至还更优选地,R1是氢或甲基。最优选地,R1是氢。
R2选自由以下各项组成的组:氢、卤素、C1-C6烷基和C1-C6卤代烷基。优选地,R2选自由以下各项组成的组:氢、卤素、C1-C6烷基和C1-C6氟烷基。更优选地,R2是氢或C1-C6烷基。甚至更优选地,R2是氢或甲基。最优选地,R2是氢。
其中当R1选自由-OR7、-OR15a、-N(R6)S(O)2R15、-N(R6)C(O)R15、-N(R6)C(O)OR15、–N(R6)C(O)NR16R17、-N(R6)CHO、-N(R7a)2和-S(O)rR15组成的组时,R2选自由以下各项组成的组:氢和C1-C6烷基。优选地,当R1选自由-OR7、-NHS(O)2R15、-NHC(O)R15、-NHC(O)OR15、-NHC(O)NR16R17、-N(R7a)2和-S(O)rR15组成的组时,R2选自由以下各项组成的组:氢和甲基。
可替代地,R1和R2与它们所附接的碳原子一起形成C3-C6环烷基环或3元至6元杂环基,该杂环基包含1或2个单独地选自N和O的杂原子。优选地,R1和R2与它们所附接的碳原子一起形成C3-C6环烷基环。更优选地,R1和R2与它们所附接的碳原子一起形成环丙基环。
在一个实施例中,R1和R2是氢。
在另一个实施例中,R1是甲基并且R2是氢。
在另一个实施例中,R1是甲基并且R2是甲基。
Q是(CR1aR2b)m。
m是0、1、2或3。优选地,m是0、1或2。更优选地,m是1或2。最优选地,m是1。
每个R1a和R2b独立地选自由以下各项组成的组:氢、卤素、C1-C6烷基、C1-C6卤代烷基、-OH、-OR7、-OR15a、-NH2、-NHR7、-NHR15a、-N(R6)CHO、-NR7bR7c以及-S(O)rR15。优选地,每个R1a和R2b独立地选自由以下各项组成的组:氢、卤素、C1-C6烷基、C1-C6氟烷基、-OH、-NH2以及-NHR7。更优选地,每个R1a和R2b独立地选自由以下各项组成的组:氢、C1-C6烷基、-OH和-NH2。甚至更优选地,每个R1a和R2b独立地选自由以下各项组成的组:氢、甲基、-OH和-NH2。甚至还更优选地,每个R1a和R2b独立地选自由以下各项组成的组:氢和甲基。最优选地,R1a和R2b是氢。
在另一个实施例中,每个R1a和R2b独立地选自由以下各项组成的组:氢和C1-C6烷基。
可替代地,每个R1a和R2b与它们所附接的碳原子一起形成C3-C6环烷基环或3元至6元杂环基,所述杂环基包含1或2个单独地选自N和O的杂原子。优选地,每个R1a和R2b与它们所附接的碳原子一起形成C3-C6环烷基环。更优选地,每个R1a和R2b与它们所附接的碳原子一起形成环丙基环。
R3、R4和R5独立地选自由以下各项组成的组:氢、氰基、硝基、C1-C6烷基、C1-C6硫代烷基、C1-C6氟烷基、C1-C6氟烷氧基、C1-C6烷氧基、C3-C6环烷基、苯基和-N(R6)2。优选地,R3、R4和R5独立地选自由以下各项组成的组:氢、C1-C6烷基、C1-C6氟烷基、C1-C6氟烷氧基、C1-C6烷氧基、C3-C6环烷基、苯基和-N(R6)2。更优选地,R3、R4和R5独立地选自由以下各项组成的组:氢、C1-C6烷基、C1-C6烷氧基和苯基。甚至更优选地,R3、R4和R5独立地选自由以下各项组成的组:氢、C1-C6烷基和苯基。甚至还更优选地,R3、R4和R5独立地选自由以下各项组成的组:氢、甲基和苯基。最优选地,R3、R4和R5是氢。
在一个实施例中,R3是氢,并且R4和R5选自由以下各项组成的组:氢、甲基和苯基。
每个R6独立地选自氢和C1-C6烷基。优选地,每个R6独立地选自氢和甲基。
每个R7独立地选自由以下各项组成的组:C1-C6烷基、-S(O)2R15、-C(O)R15、-C(O)OR15以及-C(O)NR16R17。优选地,每个R7独立地选自由以下各项组成的组:C1-C6烷基、-C(O)R15和-C(O)NR16R17。更优选地,每个R7是C1-C6烷基。最优选地,每个R7是甲基。
每个R7a独立地选自由以下各项组成的组:-S(O)2R15、-C(O)R15、-C(O)OR15、-C(O)NR16R17和-C(O)NR6R15a。优选地,每个R7a独立地是-C(O)R15或-C(O)NR16R17。
R7b和R7c独立地选自由以下各项组成的组:C1-C6烷基、-S(O)2R15、-C(O)R15、-C(O)OR15、-C(O)NR16R17和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代。优选地,R7b和R7c独立地选自由以下各项组成的组:C1-C6烷基、-C(O)R15和-C(O)NR16R17。更优选地,R7b和R7c是C1-C6烷基。最优选地,R7b和R7c是甲基。
可替代地,R7b和R7c与它们所附接的氮原子一起形成4元至6元杂环基环,其任选地包含一个另外的单独地选自N、O和S的杂原子。优选地,R7b和R7c与它们所附接的氮原子一起形成5元至6元杂环基环,其任选地包含一个另外的单独地选自N和O的杂原子。更优选地,R7b和R7c与它们所附接的氮原子一起形成吡咯烷基、噁唑烷基、咪唑烷基、哌啶基、哌嗪基或吗啉基基团。
R7d和R7e独立地选自由以下各项组成的组:氢、C1-C6烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C1-C3烷氧基C1-C3烷基-、C2-C6炔基、-S(O)2R15、-C(O)R15、-C(O)OR15、-C(O)NR16R17和苯基,并且其中所述苯基任选地被1、2或3个R9取代基取代。优选地,R7d和R7e独立地选自由以下各项组成的组:氢、C1-C6烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C1-C3烷氧基C1-C3烷基-、C2-C6炔基、-C(O)R15和-C(O)OR15。更优选地,R7d和R7e独立地选自由以下各项组成的组:氢、C1-C6烷基、C3-C6环烷基C1-C3烷基-、C1-C3烷氧基C1-C3烷基-、C2-C6炔基、-C(O)R15和-C(O)OR15。甚至更优选地,R7d和R7e独立地选自由以下各项组成的组:氢、C1-C6烷基、-C(O)R15和-C(O)OR15。甚至还更优选地,R7d和R7e独立地选自由以下各项组成的组:氢、甲基、-C(O)Me和-C(O)(OtBu)。
R8a选自由以下各项组成的组:氢、-OH、-OR7、-S(O)rR15、-C(O)OR10、-C(O)R15、-C(O)NR16R17、-S(O)2NR16R17、-NR7dR7e、R15S(O)rC1-C3烷基-、R16R17NS(O)2C1-C3烷基-、R15C(O)C1-C3烷基-、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷氧基、C3-C6环烷基C1-C3烷基-、C3-C6环烷基C1-C3烷氧基-、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、C1-C3烷氧基C1-C3烷氧基-、C1-C6卤代烷氧基、C1-C3卤代烷氧基C1-C3烷基-、C3-C6烯基氧基、C3-C6炔基氧基、-C(R6)=NOR6、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1、2或3个可以是相同或不同的R9取代基取代。
优选地,R8a选自由以下各项组成的组:-NR7dR7e、R15S(O)rC1-C3烷基-、R16R17NS(O)2C1-C3烷基-、R15C(O)C1-C3烷基-、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1、2或3个可以是相同或不同的R9取代基取代。
更优选地,R8a选自由以下各项组成的组:-NR7dR7e、R15S(O)rC1-C3烷基-、R16R17NS(O)2C1-C3烷基-、R15C(O)C1-C3烷基-、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1或2个可以是相同或不同的R9取代基取代。
甚至更优选地,R8a选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1个R9取代基取代。
甚至还更优选地,R8a选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、氰基C1-C3烷基-、苯基和杂环基,其中杂环基部分是包含1个S(O)r杂原子的4元至6元饱和或部分饱和的环,并且其中所述苯基任选地被1个R9取代基取代。
又甚至还更优选地,R8a选自由以下各项组成的组:甲基、乙基、异丙基、正丙基、正丁基、异丁基、叔丁基、2,2,2-三氟乙基-、烯丙基、炔丙基、1-甲基丙-2-炔基、1,1-二甲基丙-2-炔基、2-甲氧基乙基-、1-氰基-1-甲基-乙基-、苯基、2-羟基苯基、硫杂环丁-3-基、1-氧代硫杂环丁-3-基和1,1,-二氧代硫杂环丁-3-基。
在一个实施例中,R8a选自由以下各项组成的组:叔丁氧基羰基(甲基)氨基-、乙酰氨基、2-甲基硫烷基乙基-、2-乙基硫烷基乙基、2-甲基亚磺酰基乙基、2-乙基亚磺酰基乙基、2-甲基磺酰基乙基、2-乙基磺酰基乙基、(1-甲基-2-甲基磺酰基-乙基)、2-(二甲基氨磺酰基)乙基、2-(甲基氨磺酰基)乙基、丙酮基、3-氧代丁基、甲基、乙基、异丙基、正丙基、正丁基、异丁基、叔丁基、2,2,2-三氟乙基-、2,2,3,3,3-五氟丙基、环丙基、环戊基、环己基、环丙基甲基-、(1-甲基环丙基)、(2-甲基环丙基)、(1-乙基环丙基)、(2,2-二甲基环丙基)、[1-(三氟甲基)环丙基]、(2,2-二氟环丙基)、1-氰基环丙基-、(2-羟基-1,1-二甲基-乙基)、(2-羟基-1-甲基-乙基)、3-羟基丁基、2-羟基丙基、1-氰基乙基-、氰基甲基-、2-氰基乙基-、烯丙基、炔丙基、1-甲基丙-2-炔基、1,1-二甲基丙-2-炔基、丁-2-炔基、丁-3-炔基、2-甲氧基乙基-、(2-甲氧基-1-甲基-乙基)、2-羟基乙基-、1-氰基-1-甲基-乙基-、苯基、2-羟基苯基、(2,4-二氟苯基)、苄基、4-氟苄基、4-氰基苄基、4-三氟甲基苄基、(5,5-二甲基-4H-异噁唑-3-基)、2-(5,5-二甲基-4H-异噁唑-3-基)乙基、硫杂环丁-3-基、1-氧代硫杂环丁-3-基、1,1,-二氧代硫杂环丁-3-基、2-吡啶基甲基、2-嘧啶-2-基乙基、吡嗪-2-基、(2-甲基吡唑-3-基)、异噁唑-3-基、噻唑-2-基甲基、2-噻唑-2-基乙基、(1-甲基-1,2,4-三唑-3-基)甲基、2-(2-甲基-1,2,4-三唑-3-基)乙基和噻唑-2-基。优选地,R8a选自由以下各项组成的组:叔丁氧基羰基(甲基)氨基-、2-甲基硫烷基乙基-、甲基、乙基、异丙基、正丙基、正丁基、异丁基、叔丁基、2,2,2-三氟乙基-、环丙基、环戊基、环己基、环丙基甲基-、1-氰基环丙基-、烯丙基、炔丙基、1-甲基丙-2-炔基、1,1-二甲基丙-2-炔基、2-甲氧基乙基-、2-羟基乙基-、1-氰基-1-甲基-乙基-、苯基、2-羟基苯基、苄基、4-氟苄基、硫杂环丁-3-基、1-氧代硫杂环丁-3-基、1,1,-二氧代硫杂环丁-3-基、异噁唑-3-基和噻唑-2-基。
R8b选自由以下各项组成的组:氢、-OR7、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷氧基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、C1-C3烷氧基C1-C3烷氧基-、C1-C6卤代烷氧基、C1-C3卤代烷氧基C1-C3烷基-、C3-C6烯基氧基以及C3-C6炔基氧基。优选地,R8b选自由以下各项组成的组:氢、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-和C1-C3烷氧基C1-C3烷氧基-。更优选地,R8b选自由以下各项组成的组:氢、C1-C6烷基和C2-C3炔基。甚至更优选地,R8b选自由以下各项组成的组:氢和C1-C6烷基。甚至还更优选地,R8b选自由以下各项组成的组:氢、甲基和异丙基。
可替代地,R8a和R8b与它们所附接的氮原子一起形成4元至6元杂环基,其任选地包含1或2个另外的独立地选自N、O和S(O)r的杂原子,并且其中所述杂环基部分任选地被1或2个可以是相同或不同的R9取代基取代。优选地,R8a和R8b与它们所附接的氮原子一起形成4元至6元杂环基,其任选地包含1或2个另外的独立地选自N、O和S(O)r的杂原子,并且其中所述杂环基部分任选地被1个R9取代基取代。更优选地,R8a和R8b与它们所附接的氮原子一起形成5元至6元杂环基,其任选地包含1或2个另外的独立地选自N、O和S(O)r的杂原子,并且其中所述杂环基部分任选地被1个R9取代基取代。甚至更优选地,R8a和R8b与它们所附接的氮原子一起形成5元至6元杂环基,其任选地包含1个另外的选自N、O和S(O)r的杂原子,并且其中所述杂环基部分任选地被1个R9取代基取代。甚至还更优选地,R8a和R8b与它们所附接的氮原子一起形成选自以下的基团:甲基哌嗪基、哌啶基、吡咯烷基、吗啉基、(1-氧代-1,4-噻嗪烷-4-基)、(1,1-二氧代-1,4-噻嗪烷-4-基)和硫代吗啉基。最优选地,R8a和R8b与它们所附接的氮原子一起形成选自以下的基团:哌啶基、吡咯烷基和吗啉基。
在一个实施例中,R8a和R8b与它们所附接的氮原子一起形成5元至6元杂环基,其任选地包含1个另外的选自N、O和S(O)、优选O的杂原子。
每个R9独立地选自由以下各项组成的组:卤素、氰基、-OH、-N(R6)2、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基。优选地,每个R9独立地选自由以下各项组成的组:卤素、氰基、-OH、-N(R6)2、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基。更优选地,每个R9独立地选自由以下各项组成的组:卤素、氰基、-OH、C1-C4烷基、C1-C4烷氧基和C1-C4卤代烷基。甚至更优选地,每个R9独立地选自由以下各项组成的组:卤素、氰基、-OH和C1-C4烷基。又甚至更优选地,每个R9是氰基或-OH。
在一个实施例中,每个R9独立地选自由以下各项组成的组:氟、氰基、-OH、甲基和CF3。
X选自由以下各项组成的组:C3-C6环烷基、苯基、包含1、2、3或4个单独地选自N、O和S的杂原子的5元或6元杂芳基以及包含1、2或3个单独地选自N、O和S的杂原子的4元至6元杂环基,并且其中所述环烷基、苯基、杂芳基或杂环基部分任选地被1或2个选自R9的可以是相同或不同的取代基取代,并且其中前述CR1R2、Q和Z部分可以附接在所述环烷基、苯基、杂芳基或杂环基部分的任何位置。
优选地,X选自由以下各项组成的组:苯基和包含1或2个单独地选自N和O的杂原子的4元至6元杂环基,并且其中所述苯基或杂环基部分任选地被1或2个选自R9的可以是相同或不同的取代基取代,并且其中前述CR1R2、Q和Z部分可以附接在所述苯基或杂环基部分的任何位置。
更优选地,X是包含1或2个单独地选自N和O的杂原子的4元至6元杂环基,并且其中所述杂环基部分任选地被1或2个选自R9的可以是相同或不同的取代基取代,并且其中前述CR1R2、Q和Z部分可以附接在所述杂环基部分的任何位置。
在一个实施例中,X是包含1个杂原子的5元杂环基,其中所述杂原子是N,并且其中前述CR1R2、Q和Z部分可以附接在所述杂环基部分的任何位置。优选地,X是包含1个杂原子的5元杂环基,其中所述杂原子是N,并且其中前述CR1R2和Q部分与N原子相邻附接并且Z部分与N原子附接。
在另一个实施例中,X是任选地被1或2个选自R9的可以是相同或不同的取代基取代的苯基,并且其中前述CR1R2、Q和Z部分可以附接在所述苯基部分的任何位置。优选地,X是苯基,并且前述CR1R2和Q部分在相对于Z部分的对位附接。
n是0或1。优选地,n为0。
Z选自由以下各项组成的组:-C(O)OR10、-CH2OH、-CHO、-C(O)NHOR11、-C(O)NHCN、-OC(O)NHOR11、-OC(O)NHCN、-NR6C(O)NHOR11、-NR6C(O)NHCN、-C(O)NHS(O)2R12、-OC(O)NHS(O)2R12、-NR6C(O)NHS(O)2R12、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10、-NR6S(O)OR10、-NHS(O)2R14、-S(O)OR10、-OS(O)OR10、-S(O)2NHCN、-S(O)2NHC(O)R18、-S(O)2NHS(O)2R12、-OS(O)2NHCN、-OS(O)2NHS(O)2R12、-OS(O)2NHC(O)R18、-NR6S(O)2NHCN、-NR6S(O)2NHC(O)R18、-N(OH)C(O)R15、-ONHC(O)R15、-NR6S(O)2NHS(O)2R12、-P(O)(R13)(OR10)、-P(O)H(OR10)、-OP(O)(R13)(OR10)、-NR6P(O)(R13)(OR10)和四唑。
优选地,Z选自由以下各项组成的组:-C(O)OR10、-C(O)NHOR11、-OC(O)NHOR11、-NR6C(O)NHOR11、-C(O)NHS(O)2R12、-OC(O)NHS(O)2R12、-NR6C(O)NHS(O)2R12、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10、-NR6S(O)OR10、-NHS(O)2R14、-S(O)OR10、-OS(O)OR10、-S(O)2NHC(O)R18、-S(O)2NHS(O)2R12、-OS(O)2NHS(O)2R12、-OS(O)2NHC(O)R18、-NR6S(O)2NHC(O)R18、-N(OH)C(O)R15、-ONHC(O)R15、-NR6S(O)2NHS(O)2R12、-P(O)(R13)(OR10)、-P(O)H(OR10)、-OP(O)(R13)(OR10)以及-NR6P(O)(R13)(OR10)。
更优选地,Z选自由以下各项组成的组:-C(O)OR10、-C(O)NHOR11、-C(O)NHS(O)2R12、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10、-NHS(O)2R14、-S(O)OR10以及-P(O)(R13)(OR10)。
甚至更优选地,Z选自由以下各项组成的组:-C(O)OR10、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10、-NHS(O)2R14和-P(O)(R13)(OR10)。
甚至还更优选地,Z选自由以下各项组成的组:-C(O)OR10、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10和-NHS(O)2R14。
又甚至还更优选地,Z选自由以下各项组成的组:-C(O)OH、-C(O)OCH3、-S(O)2OH、-OS(O)2OH、-NHS(O)2OH和-NHS(O)2CF3。
最优选地,Z是-C(O)OH或-S(O)2OH。
在一个实施例中,Z选自由以下各项组成的组:-C(O)OH、-C(O)OCH3、-S(O)2OH、-OS(O)2OH、-NHS(O)2OH、NHS(O)2CF3、-P(O)(OCH2CH3)(OCH2CH3)和-P(O)(OH)(OH)。
R10选自由以下各项组成的组:氢、C1-C6烷基、苯基以及苄基,并且其中所述苯基或苄基任选地被1、2或3个可以是相同或不同的R9取代基取代。优选地,R10选自由以下各项组成的组:氢、C1-C6烷基、苯基以及苄基。更优选地,R10选自由以下各项组成的组:氢和C1-C6烷基。最优选地,R10是氢。
R11选自由以下各项组成的组:氢、C1-C6烷基和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代。优选地,R11选自由以下各项组成的组:氢、C1-C6烷基和苯基。更优选地,R11选自由以下各项组成的组:氢和C1-C6烷基。甚至更优选地,R11是C1-C6烷基。最优选地,R11是甲基。
R12选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、-OH、-N(R6)2以及苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代。优选地,R12选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、-OH、-N(R6)2以及苯基。更优选地,R12选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基和-N(R6)2。甚至更优选地,R12选自由以下各项组成的组:甲基、-N(Me)2和三氟甲基。最优选地,R12是甲基。
R13选自由以下各项组成的组:-OH、C1-C6烷基、C1-C6烷氧基和苯基。优选地,R13选自由以下各项组成的组:-OH、C1-C6烷基和C1-C6烷氧基。更优选地,R13选自由以下各项组成的组:-OH和C1-C6烷氧基。甚至更优选地,R13选自由以下各项组成的组:-OH、甲氧基和乙氧基。最优选地,R13是-OH。
R14是C1-C6卤代烷基。优选地,R14是三氟甲基。
R15选自由以下各项组成的组:C1-C6烷基和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代。优选地,R15选自由以下各项组成的组:C1-C6烷基和苯基。更优选地,R15是C1-C6烷基。甚至更优选地,R15是甲基或乙基。最优选地,R15是甲基。
R15a是苯基,其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代。优选地,R15a是任选地被1个R9取代基取代的苯基。更优选地,R15a是苯基。
R16和R17独立地选自由以下各项组成的组:氢和C1-C6烷基。优选地,R16和R17独立地选自由以下各项组成的组:氢和甲基。
可替代地,R16和R17与它们所附接的氮原子一起形成4元至6元杂环基环,其任选地包含一个另外的单独地选自N、O和S的杂原子。优选地,R16和R17与它们所附接的氮原子一起形成5元至6元杂环基环,其任选地包含一个另外的单独地选自N和O的杂原子。更优选地,R16和R17与它们所附接的氮原子一起形成吡咯烷基、噁唑烷基、咪唑烷基、哌啶基、哌嗪基或吗啉基基团。
R18选自由以下各项组成的组:氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、-N(R6)2以及苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代。优选地,R18选自由以下各项组成的组:氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、-N(R6)2以及苯基。更优选地,R18选自由以下各项组成的组:氢、C1-C6烷基和C1-C6卤代烷基。进一步更优选地,R18选自由以下各项组成的组:C1-C6烷基和C1-C6卤代烷基。最优选地,R18是甲基或三氟甲基。
r是0、1或2。优选地,r是0或2。
在一组优选实施例中,在本发明的根据式(I)的化合物中,
R1是氢或C1-C6烷基;
R2是氢或甲基;
Q是(CR1aR2b)m;
m是0、1或2;
R1a和R2b独立地选自由以下各项组成的组:氢、C1-C6烷基、-OH和-NH2;
R3、R4和R5独立地选自由以下各项组成的组:氢、C1-C6烷基和苯基;
每个R6独立地选自氢和甲基;
R7d和R7e独立地选自由以下各项组成的组:氢、C1-C6烷基、-C(O)R15和-C(O)OR15;
R8a选自由以下各项组成的组:-NR7dR7e、R15S(O)rC1-C3烷基-、R16R17NS(O)2C1-C3烷基-、R15C(O)C1-C3烷基-、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1或2个可以是相同或不同的R9取代基取代;
R8b选自由以下各项组成的组:氢、C1-C6烷基和C2-C3炔基;或者
R8a和R8b与它们所附接的氮原子一起形成4元至6元杂环基,其任选地包含1或2个另外的独立地选自N、O和S(O)r的杂原子,并且其中所述杂环基部分任选地被1个R9取代基取代;并且
R9独立地选自由以下各项组成的组:卤素、氰基、-OH、C1-C4烷基、C1-C4烷氧基和C1-C4卤代烷基;
n是0;
Z选自由以下各项组成的组:-C(O)OR10、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10、-NHS(O)2R14和-P(O)(R13)(OR10);
R10选自由以下各项组成的组:氢、C1-C6烷基、苯基和苄基;
R13选自由以下各项组成的组:-OH和C1-C6烷氧基;
R14是三氟甲基;
R15是C1-C6烷基;
R16和R17独立地选自由以下各项组成的组:氢和甲基;并且
r是0、1或2。
优选地,
R1是氢或甲基;
R2是氢或甲基;
Q是(CR1aR2b)m;
m是0、1或2;
R1a和R2b独立地选自由以下各项组成的组:氢、甲基、-OH和-NH2;
R3、R4和R5独立地选自由以下各项组成的组:氢、甲基和苯基;
每个R6独立地选自氢和甲基;
R7d和R7e独立地选自由以下各项组成的组:氢、甲基、-C(O)Me和-C(O)(OtBu);
R8a选自由以下各项组成的组:-NR7dR7e、R15S(O)rC1-C3烷基-、R16R17NS(O)2C1-C3烷基-、R15C(O)C1-C3烷基-、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1或2个可以是相同或不同的R9取代基取代;
R8b选自由以下各项组成的组:氢、甲基和异丙基;或者
R8a和R8b与它们所附接的氮原子一起形成5元至6元杂环基,其任选地包含1或2个另外的独立地选自N、O和S(O)r的杂原子,并且其中所述杂环基部分任选地被1个R9取代基取代;并且
R9独立地选自由以下各项组成的组:氟、氰基、-OH、甲基和CF3;
n是0;
Z选自由以下各项组成的组:-C(O)OH、-C(O)OCH3、-S(O)2OH、-OS(O)2OH、-NHS(O)2OH、NHS(O)2CF3、-P(O)(OCH2CH3)(OCH2CH3)和-P(O)(OH)(OH);
R15是甲基或乙基;
R16和R17独立地选自由以下各项组成的组:氢和甲基;并且
r是0、1或2。
在另一组优选实施例中,在本发明的根据式(I)的化合物中:
R1是氢或C1-C6烷基;
R2是氢或甲基;
Q是(CR1aR2b)m;
m是0、1或2;
R1a和R2b独立地选自由以下各项组成的组:氢、C1-C6烷基、-OH和-NH2;
R3、R4和R5独立地选自由以下各项组成的组:氢、C1-C6烷基和苯基;
每个R6独立地选自氢和甲基;
R8a选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1个R9取代基取代;
R8b选自由以下各项组成的组:氢、C1-C6烷基和C2-C3炔基;或者
R8a和R8b与它们所附接的氮原子一起形成5元至6元杂环基,其任选地包含1个另外的O杂原子;并且
R9独立地选自由以下各项组成的组:卤素、氰基、-OH和C1-C4烷基;
n是0;
Z选自由以下各项组成的组:-C(O)OR10、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10和-NHS(O)2R14;
R10选自由以下各项组成的组:氢、C1-C6烷基、苯基和苄基;
R14是三氟甲基;并且
r是0、1或2。
优选地,
R1是氢或甲基;
R2是氢或甲基;
Q是(CR1aR2b)m;
m是1或2;
R1a和R2b独立地选自由以下各项组成的组:氢和甲基;
R3、R4和R5独立地选自由以下各项组成的组:氢、甲基和苯基;
每个R6独立地选自氢和甲基;
R8a选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、氰基C1-C3烷基-、苯基和杂环基,其中杂环基部分是包含1个S(O)r杂原子的4元至6元饱和或部分饱和的环,并且其中所述苯基任选地被1个R9取代基取代;
R8b选自由以下各项组成的组:氢和C1-C6烷基;
R9是氰基或-OH;
n是0;并且
Z选自由以下各项组成的组:C(O)OH、-C(O)OCH3、-S(O)2OH、-OS(O)2OH、-NHS(O)2OH和-NHS(O)2CF3。
在一组优选实施例中,根据式(I)的化合物选自具有式(I-a)、(I-b)、(I-c)、(I-d)、(I-e)、(I-f)或(I-g)的化合物,
其中在具有式(I-a)、(I-b)、(I-c)、(I-d)、(I-e)、(I-f)或(I-g)的化合物中,
R8a选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、氰基C1-C3烷基-、苯基和杂环基,其中杂环基部分是包含1个S(O)r杂原子的4元至6元饱和或部分饱和的环,并且其中所述苯基任选地被1个R9取代基取代;
R8b选自由以下各项组成的组:氢和C1-C6烷基;
R9是氰基或-OH;并且
Z选自由以下各项组成的组:C(O)OH、-C(O)OCH3、-S(O)2OH、-OS(O)2OH、-NHS(O)2OH和-NHS(O)2CF3。
在另一组实施例中,根据式(I)的化合物选自表A中列出的化合物A1至A148。
应当理解,具有式(I)的化合物能以‘procidal形式’存在/制造,其中它们包含基团‘G’。此类化合物在本文中称为具有式(I-IV)的化合物。
G是可以通过任何适当的机制在植物中除去的基团,该机制包括但不限于代谢和化学降解,以给出具有式(I-I)、(I-II)或(I-III)的化合物,其中Z含有酸性质子,例如参见下面的方案:
当此类G基团可以被认为是“procidal”,并且因此一旦除去就产生活性除草化合物时,包含此类基团的化合物本身也可以展现出除草活性。在此类情况下,在具有式(I-IV)的化合物中,Z-G可以包括但不限于下面的(G1)至(G7)中的任何一个,并且E指示与具有式(I)的化合物的剩余部分的附接点:
在其中Z-G为(G1)至(G7)的实施例中,G、R19、R20、R21、R22和R23是如下所定义的:
G是C1-C6烷基、C2-C6烯基、C2-C6炔基、-C(R21R22)OC(O)R19、苯基或苯基-C1-C4烷基-,其中所述苯基部分任选地被1至5个独立地选自卤基、氰基、硝基、C1-C6烷基、C1-C6卤代烷基或C1-C6烷氧基的取代基取代。
R19是C1-C6烷基或苯基,
R20是羟基、C1-C6烷基、C1-C6烷氧基或苯基,
R21是氢或甲基,
R22是氢或甲基,
R23是氢或C1-C6烷基。
以下表1至表20中的化合物阐明本发明的化合物。技术人员将理解,具有式(I)的化合物可以如上文所述的作为农艺学上可接受的盐、两性离子或农艺学上可接受的两性离子盐存在。
表1:此表披露了53种具体的具有式(T-1)的化合物:
其中m、Q、R3、R4、R5和Z是如表1中所定义的,R1和R2是氢,并且n是0。
表2:
此表披露了49种具体的具有式(T-2)的化合物:
其中m、Q、R3、R4、R5和Z是如表2中所定义的,R1和R2是氢,并且n是0。
表3:
此表披露了49种具体的具有式(T-3)的化合物:
其中m、Q、R3、R4、R5和Z是如表3中所定义的,R1和R2是氢,并且n是0。
表4:
此表披露了53种具体的具有式(T-4)的化合物:
其中m、Q、R3、R4、R5和Z是如上表1中所定义的,R1和R2是氢,并且n是0。
表5:
此表披露了49种具体的具有式(T-5)的化合物:
其中m、Q、R3、R4、R5和Z是如上表2中所定义的,R1和R2是氢,并且n是0。
表6:
此表披露了49种具体的具有式(T-6)的化合物:
其中m、Q、R3、R4、R5和Z是如上表3中所定义的,R1和R2是氢,并且n是0。
表7:
此表披露了53种具体的具有式(T-7)的化合物:
其中m、Q、R3、R4、R5和Z是如上表1中所定义的,R1和R2是氢,并且n是0。
表8:
此表披露了49种具体的具有式(T-8)的化合物:
其中m、Q、R3、R4、R5和Z是如上表2中所定义的,R1和R2是氢,并且n是0。
表9:
此表披露了49种具体的具有式(T-9)的化合物:
其中m、Q、R3、R4、R5和Z是如上表3中所定义的,R1和R2是氢,并且n是0。
表10:
此表披露了53种具体的具有式(T-10)的化合物:
其中m、Q、R3、R4、R5和Z是如上表1中所定义的,R1和R2是氢,并且n是0。
表11:
此表披露了49种具体的具有式(T-11)的化合物:
其中m、Q、R3、R4、R5和Z是如上表2中所定义的,R1和R2是氢,并且n是0。
表12:
此表披露了49种具体的具有式(T-12)的化合物:
其中m、Q、R3、R4、R5和Z是如上表3中所定义的,R1和R2是氢,并且n是0。
表13:
此表披露了53种具体的具有式(T-13)的化合物:
其中m、Q、R3、R4、R5和Z是如上表1中所定义的,R1和R2是氢,并且n是0。
表14:
此表披露了49种具体的具有式(T-14)的化合物:
其中m、Q、R3、R4、R5和Z是如上表2中所定义的,R1和R2是氢,并且n是0。
表15:
此表披露了49种具体的具有式(T-15)的化合物:
其中m、Q、R3、R4、R5和Z是如上表3中所定义的,R1和R2是氢,并且n是0。
表16:
此表披露了53种具体的具有式(T-16)的化合物:
其中m、Q、R3、R4、R5和Z是如上表1中所定义的,R1和R2是氢,并且n是0。
表17:
此表披露了49种具体的具有式(T-17)的化合物:
其中m、Q、R3、R4、R5和Z是如上表2中所定义的,R1和R2是氢,并且n是0。
表18:
此表披露了49种具体的具有式(T-18)的化合物:
其中m、Q、R3、R4、R5和Z是如上表3中所定义的,R1和R2是氢,并且n是0。
表19:
此表披露了17种具体的具有式(T-19)的化合物:
其中R8a和R8b是如表19中所定义的,R3、R4和R5是氢。
表20:
此表披露了17种具体的具有式(T-20)的化合物:
其中R8a和R8b是如表20中所定义的,R3、R4和R5是氢。
本发明的化合物可以根据下列方案制备,其中除非另外明确说明,取代基n、m、r、Q、X、Z、R1、R2、R1a、R2b、R2、R3、R4、R5、R6、R7、R7a、R7b、R7c、R7d、R7e、R8a、R8b、R9、R10、R11、R12、R13、R14、R15、R15a、R16、R17和R18如上文所定义。因此,前述表1至表20的化合物能以类似的方式获得。
具有式(I)的化合物可以通过在合适的温度下,在合适的溶剂中,将具有式(X)化合物(其中R3、R4、R5、R8a和R8b是如针对具有式(I)的化合物所定义的)用具有式(W)的合适烷基化剂(其中R1、R2、Q、X、n和Z是如针对具有式(I)的化合物所定义的,并且LG是合适的离去基团,例如卤化物或拟卤化物,如三氟甲磺酸酯、甲磺酸酯或甲苯磺酸酯)烷基化来制备,如反应方案1中所述。示例性条件包括在-78℃与150℃之间的温度下,将具有式(X)的化合物与具有式(W)的烷基化剂在如丙酮、二氯甲烷、二氯乙烷、N,N-二甲基甲酰胺、乙腈、1,4-二噁烷、水、乙酸或三氟乙酸等溶剂或溶剂混合物中进行搅拌。具有式(W)的烷基化剂是可商购获得的或在文献中是已知的,并且可以包括但不限于溴乙酸、溴乙酸甲酯、3-溴丙酸、3-溴丙酸甲酯、2-溴-N-甲氧基乙酰胺、2-溴乙磺酸钠、2-(三氟甲基磺酰氧基)乙磺酸2,2-二甲基丙酯、2-溴-N-甲磺酰基乙酰胺、3-溴-N-甲磺酰基丙酰胺、三氟甲磺酸二甲氧基磷酰基甲酯、3-溴丙基膦酸二甲酯、3-氯-2,2-二甲基-丙酸和2-溴乙基膦酸二乙酯。此类烷基化剂和相关化合物在文献中是已知的,或者可以通过已知的文献方法制备。随后可以将可描述为N-烷基酸的酯(其包括但不限于羧酸、膦酸、次膦酸、磺酸和亚磺酸的酯)的具有式(I)的化合物通过在0℃与100℃之间的合适温度下,在合适的溶剂中,用合适的试剂(例如,水性盐酸或三甲基甲硅烷基溴化物)进行处理来部分或完全水解。
反应方案1
另外,具有式(I)的化合物可以通过在合适的温度下,在合适的溶剂中,使具有式(X)的化合物(其中R3、R4、R5、R8a和R8b是如针对具有式(I)的化合物所定义的)与适当活化的具有式(B)的亲电子烯烃(其中R1、R2和R1a是如针对具有式(I)的化合物所定义的并且Z是-S(O)2OR10、-P(O)(R13)(OR10)或-C(O)OR10)反应来制备,如反应方案2中所述。合适的溶剂和合适的温度如先前所述。具有式(B)的化合物在文献中是已知的,或者可以通过已知的方法制备。示例性试剂包括但不限于丙烯酸、甲基丙烯酸、巴豆酸、3,3-二甲基丙烯酸、丙烯酸甲酯、乙烯磺酸、乙烯磺酸异丙酯、乙烯磺酸2,2-二甲基丙酯和乙烯基膦酸二甲酯。随后可以将可描述为N-烷基酸的酯(其包括但不限于羧酸、膦酸、次膦酸、磺酸和亚磺酸的酯)的这些反应的直接产物通过在合适的温度下,在合适的溶剂中,用合适的试剂进行处理来部分或完全水解,如反应方案2中所述。
反应方案2
在相关的反应中,具有式(I)的化合物(其中Q是C(R1aR2b),m是1、2或3,n=0并且Z是-S(O)2OH、-OS(O)2OH或-NR6S(O)2OR10)可以通过在合适的温度下,在合适的溶剂中,使具有式(X)的化合物(其中R3、R4、R5、R8a和R8b是如针对具有式(I)的化合物所定义的)与具有式(E)、(F)或(AF)的环状烷基化剂(其中Y是C(R1aR2b)、O或NR6,并且R1、R2、R1a和R2b是如针对具有式(I)的化合物所定义的)反应来制备,如反应方案3中所述。合适的溶剂和合适的温度如先前所述。具有式(E)或(F)的烷基化剂可以包括但不限于1,3-丙磺酸内酯、1,4-丁磺酸内酯、乙烯磺酸酯、1,3-丙烯硫酸酯和1,2,3-噁噻唑烷2,2-二氧化物。此类烷基化剂和相关化合物在文献中是已知的,或者可以通过已知的文献方法制备。
反应方案3
具有式(I)的化合物(其中m是0,n是0,Z是-S(O)2OH,并且R3、R4、R5、R8a和R8b是如针对具有式(I)的化合物所定义的)可以由具有式(I)的化合物(其中m是0,n是0并且Z是C(O)OR10),通过在合适的温度下,在合适的溶剂中,用三甲基甲硅烷基氯磺酸酯进行处理来制备,如反应方案4中所述。优选的条件包括在25℃与150℃之间的温度下在纯三甲基甲硅烷基氯磺酸酯中加热羧酸酯前体。
反应方案4
此外,具有式(I)的化合物可以通过使具有式(X)的化合物(其中R3、R4、R5、R8a和R8b是如针对具有式(I)的化合物所定义的)与具有式(WW)的合适醇(其中R1、R2、Q、X、n和Z是如针对具有式(I)的化合物所定义的)在光延反应(Mitsunobu)类型条件(如Petit等人,Tet.Lett.[四面体快报]2008,49(22),3663报告的那些)下反应来制备,如反应方案5中所述。合适的膦包括三苯基膦,合适的偶氮二羧酸酯包括偶氮二羧酸二异丙酯,并且合适的酸包括氟硼酸、三氟甲磺酸和双(三氟甲基磺酰基)胺。具有式(WW)的醇在文献中是已知的或者可以通过已知的文献方法制备或者可以是可商购的。
反应方案5
具有式(I)的化合物还可以通过使具有式(C)的化合物(其中R3、R4、R5、R8a和R8b是如针对具有式(I)的化合物所定义的,并且R'是H、C1-C4烷基或C1-C4烷基羰基)在合适的温度(-78℃与150℃之间)下,在合适的酸存在下,在合适的溶剂或溶剂混合物中与具有式(D)(其中R1、R2、Q、X、n和Z是如针对具有式(I)的化合物所定义的)的肼反应来制备,如反应方案6中所述。合适的溶剂或其混合物包括但不限于醇(如甲醇、乙醇和异丙醇)、水、水性盐酸、水性硫酸、乙酸和三氟乙酸。具有式(D)的肼化合物(例如2-肼基乙磺酸2,2-二甲基丙酯或3-肼基丙酸乙酯)在文献中是已知的,或者可以通过已知的文献方法制备。
反应方案6
具有式(C)的化合物可以通过在合适的温度(-78℃与150℃之间)下,任选地在合适的碱存在下,在合适的溶剂中,使具有式(G)的化合物(其中R3、R4、R5、R8a和R8b是如针对具有式(I)的化合物所定义的)与氧化剂反应来制备,如反应方案7中所述。合适的氧化剂包括但不限于溴,并且合适的溶剂包括但不限于醇,如甲醇、乙醇和异丙醇。合适的碱包括但不限于碳酸氢钠、碳酸钠、碳酸氢钾、碳酸钾和乙酸钾。类似的反应在文献中是已知的(例如Hufford,D.L.;Tarbell,D.S.;Koszalka,T.R.J.Amer.Chem.Soc.[美国化学学会杂志],1952,3014)。具有式(G)的呋喃在文献中是已知的,或者可以使用文献方法制备。
反应方案7
具有式(X)的化合物可以通过经典的酰胺键形成反应(其在文献中是非常熟知的)来制备。实例包括但不限于在合适的温度(-78℃与200℃之间)下,任选地在合适的碱存在下,在合适的溶剂或溶剂混合物中,使具有式(K)的胺(其中R8a和R8b是如先前定义的)与具有式(J)的酸卤化物(其中T是卤素并且R3、R4和R5是如先前所定义的)反应。
在替代性方法中,具有式(X)的化合物可以通过使具有式(K)的胺与具有式(J)的酯或活化酯反应来制备,其中T是例如-OC1-C6烷基、五氟苯酚、对硝基苯酚、2,4,6-三氯苯酚、-OC(O)R“‘或-OS(O)2R“‘,并且R“‘是例如C1-C6烷基、C1-C6卤代烷基或任选取代的苯基。此类反应在-78℃与200℃之间的合适温度下在合适的溶剂或溶剂混合物中并且任选地在合适的碱存在下进行。合适的碱包括但不限于三乙胺,吡啶,N,N-二异丙基乙胺,碱金属碳酸盐,如碳酸钠、碳酸钾或碳酸铯,或碱金属醇盐,如甲醇钠。合适的溶剂包括但不限于二氯甲烷、N,N-二甲基甲酰胺、THF或甲苯。这些反应在方案8中描述。具有式(J)和式(K)的化合物在文献中是已知的或者可以通过已知的文献方法制备或者可以是可商购的。
反应方案8
在另外的方法中,具有式(X)的化合物可以在-78℃与200℃之间的合适温度下并且任选地在合适的碱存在下,在合适的溶剂或溶剂混合物中,在合适的偶联剂存在下由如先前所述的具有式(K)的胺和具有式(L)的羧酸制备,其中R3、R4和R5是如针对具有式(I)的化合物所定义的。合适的偶联剂包括但不限于碳二亚胺,例如二环己基碳二亚胺或1-乙基-3-[3-二甲基氨基丙基]碳二亚胺盐酸盐,膦酸酐,例如2,4,6-三丙基-1,3,5,2,4,6-三氧杂三磷杂环己烷-2,4,6-三氧化物或鏻盐,例如苯并三唑-1-基氧基(三吡咯烷-1-基)鏻六氟磷酸盐。合适的溶剂包括但不限于二氯甲烷、N,N-二甲基甲酰胺、THF或甲苯,并且合适的碱包括但不限于三乙胺、吡啶和N,N-二异丙基乙胺。此反应在方案9中描述。具有式(L)的化合物在文献中是已知的或者可以通过已知的文献方法制备或者可以是可商购的。
反应方案9
如先前所述的具有式(X)的化合物可以在合适的温度下,在合适的溶剂中,由具有式(P)和式(O)的化合物制备,如反应方案10中所概述的。这种反应的实例在文献中是已知的,例如,WO 2001038332。具有式(P)和式(O)的化合物在文献中是已知的,或者可以通过已知的方法制备。
反应方案10
如先前定义的具有式(X)的化合物也可以通过具有式(ZZ)的化合物的氨基羰基化来制备,其中Hal被定义为卤素或拟卤素,例如三氟甲磺酸酯、甲磺酸酯和甲苯磺酸酯。示例性条件包括但不限于在合适的温度和压力下,在合适的溶剂中,在合适的过渡金属、合适的碱存在下,使具有式(ZZ)的化合物与具有式(K)的胺反应。此类反应在文献中是已知的,例如Wang,J.Y.,Strom,A.E.,Hartwig,J.F.,J.Am.Chem.Soc.[美国化学会志]2018,140,7979。
反应方案11
在反应方案12中概括的方法中,具有式(X)的化合物(其中R8a和R8b是如先前所定义的)可以由具有式(Q)的化合物制备,其中W是可以通过一个或多个化学步骤转化为酰胺的官能团。此类官能团包括但不限于腈、卤素、醛和肟。这些官能团向酰胺的转化在文献中是熟知的。具有式(Q)的化合物在文献中是已知的,或者可以通过已知方法制备。
反应方案12
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。这些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可以使用前稀释再使用。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品佐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。这些活性成分还可以与其他佐剂(例如精细分散固体、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。
这些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值释放(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%。这些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这些组合物的配制佐剂本身是已知的。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,例如戊醇、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。典型的表面活性物质包括例如烷基硫酸酯的盐,如十二烷基硫酸二乙醇铵;烷基芳基磺酸酯的盐,如十二烷基苯磺酸钙;烷基酚/氧化烯加成产物,如乙氧基化壬基苯酚;醇/氧化烯加成产物,如乙氧基化十三烷醇;皂,如硬脂酸钠;烷基萘磺酸酯的盐,如二丁基萘磺酸钠;磺基琥珀酸二烷基酯的盐,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,如氯化十二烷基三甲基铵;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;以及磷酸单烷基酯和二烷基酯的盐;以及还有其他物质,例如描述于:McCutcheon'sDetergents and Emulsifiers Annual[麦卡琴清洁剂和乳化剂年鉴],MC出版公司(MCPublishing Corp.),里奇伍德,新泽西州(Ridgewood New Jersey)(1981)。
可以用于杀有害生物配制品的其他佐剂包括结晶抑制剂、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,该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该待施用的混合物的从0.01%至10%。例如,可以在喷雾混合物已经制备之后将该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)。许多油衍生物获知于Compendium of Herbicide Adjuvants[除草剂佐剂纲要],第10版,南伊利诺伊大学,2010。
这些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,该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%的配制佐剂,该配制佐剂优选地包括按重量计从0至25%的表面活性物质。而商用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。
施用比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、施用时间以及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%
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,该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。此类混合物的特定实例包括(其中“I”代表具有式(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+氟丁酰草胺-M、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、敌草隆、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+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+2-[[3-[2-氯-4-氟-5-[3-甲基-2,6-二氧代-4-(三氟甲基)嘧啶-1-基]苯氧基]-2-吡啶基]氧基]乙酸乙酯、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]咪唑啉-2-酮、I+4-羟基-1,5-二甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、I+5-乙氧基-4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、I+4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、I+4-羟基-1,5-二甲基-3-[1-甲基-5-(三氟甲基)吡唑-3-基]咪唑啉-2-酮、I+(4R)1-(5-叔丁基异噁唑-3-基)-4-乙氧基-5-羟基-3-甲基-咪唑啉-2-酮、I+3-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]二环[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]二环[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)。
具有式(I)的化合物的混合配伍物还可以呈酯或盐的形式,例如在以下文献中所提到的:The Pesticide Manual[杀有害生物剂手册],第十四版,英国作物保护委员会(British Crop Protection Council),2006。
具有式(I)的化合物还可以以与其他农用化学品(如杀真菌剂、杀线虫剂或杀昆虫剂)的混合物使用,其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这些配制品中(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);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+解草恶唑、I+双苯噁唑酸(包括双苯噁唑酸-乙基);I+吡唑解草酸(包括吡唑解草酯);I+metcamifen;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呈酯或盐的形式,如例如在The PesticideManual[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-抑制剂和HPPD-抑制剂)的抗性的那些作物。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)的抗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对除草剂的抗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,所述玉米品种在商标名和下是可商购的。
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毒素是由苏云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于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,种子可以具有表达杀昆虫的Cry3蛋白的能力,而同时是抗草甘膦的。
作物还应被理解为包括通过常规的育种方法或基因工程方法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(Abutilon theophrasti)、反枝苋(Amaranthus retroflexus)、鬼针草(Bidens pilosa)、藜草(Chenopodium album)、白苞猩猩草(Euphorbiaheterophylla)、猪殃殃(Galium aparine)、牵牛花(Ipomoea hederacea)、地肤(Kochiascoparia)、卷茎蓼(Polygonum convolvulus)、刺金午时花(Sida spinosa)、新疆野生油菜(Sinapis arvensis)、龙葵(Solanum nigrum)、繁缕(Stellaria media)、波斯婆婆纳(Veronica persica)和苍耳(Xanthium strumarium)。
具有式(I)的化合物也可用于作物收获前干燥,例如但不限于马铃薯、大豆、向日葵和棉花。收获前干燥用于干燥作物叶片,而不会对作物本身造成显著损害,以帮助收获。
本发明的化合物/组合物特别可用于非选择性燃尽(burn-down)应用,并且因此也可用于控制自生自长(volunteer)或逃逸作物(escape crop)植物。
现在将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。
实例
以下实例用来说明但不限制本发明。
配制品实例
将该组合与这些佐剂充分混合并且将混合物在适当的研磨机中充分研磨,从而获得了可以用水稀释而给出所希望的浓度的悬浮液的可湿性粉剂。
可乳化的浓缩物
在植物保护中可以使用的具有任何所要求的稀释的乳液可以通过用水稀释从这种浓缩物中获得。
通过将该组合与载体混合并且将混合物在适当的研磨机中研磨而获得即用型尘剂。
挤出机颗粒
将该组合与这些佐剂混合并且研磨,并且将混合物用水湿润。将混合物挤出并且然后在空气流中干燥。
包衣的颗粒
活性成分 8%
聚乙二醇(分子量200) 3%
高岭土 89%
将这种精细研磨的组合在混合器中均匀地施用于用聚乙二醇湿润的高岭土中。以此方式获得无尘的包衣的颗粒。
悬浮液浓缩物
将精细地研磨的组合与佐剂紧密地混合,得到悬浮液浓缩物,从该悬浮液浓缩液可以通过用水稀释获得任何所希望的稀释度的悬浮液。
缓释的胶囊悬浮液
将28份的组合与2份的芳香族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-聚苯基异氰酸酯-混合物(8:1)进行混合。将此混合物在1.2份的聚乙烯醇、0.05份的消泡剂以及51.6份的水的混合物中进行乳化直至达到所希望的粒度。向此乳液中添加在5.3份的水中的2.8份的1,6-己二胺混合物。将混合物搅拌直至聚合反应完成。
将获得的胶囊悬浮液通过添加0.25份的增稠剂以及3份的分散剂进行稳定。该胶囊悬浮液配制品包含28%的活性成分。该介质胶囊的直径是8微米-15微米。
将所得配制品作为适用于此目的装置中的水性悬浮液施用到种子上。
缩写列表:
Boc =叔丁氧基羰基
br =宽峰
CDCl3 =氯仿-d
CD3OD =甲醇-d
℃ \=摄氏度
D2O =水-d
DCM =二氯甲烷
d =二重峰
dd =双二重峰
dt =双三重峰
DMSO =二甲基亚砜
EtOAc =乙酸乙酯
h =小时
HCl =盐酸
HPLC =高效液相色谱法(下面给出了用于HPLC的装置和方法的描述)
m =多重峰
M =摩尔
min =分钟
MHz =兆赫兹
mL =毫升
mp =熔点
ppm =百万分率
q =四重峰
quin =五重峰
rt =室温
s =单峰
t =三重峰
THF =四氢呋喃
LC/MS =液相色谱质谱法
制备型反相HPLC方法:
将化合物在Waters FractionLynx Autopurification系统上使用ES+/ES-通过质量定向的制备型HPLC纯化,该系统包括具有2545梯度泵的2767注射器/收集器、两个515等度泵、SFO、2998光电二极管阵列(波长范围(nm):210至400)、2424ELSD和QDa质谱仪。WatersAtlantis T3 5微米19×10mm保护柱与Waters Atlantis T3OBD,5微米30×100mm制备柱一起使用。
电离方法:电喷雾正和负:锥孔(V)20.00,源温度(℃)120,锥孔气流量(L/Hr.)50
质量范围(Da):正100至800,负115至800。
根据以下梯度表,利用11.4分钟运行时间来进行制备型HPLC(不使用在柱稀释,用柱选择器绕开):
515泵,0ml/min乙腈(ACD)
515泵,1ml/min 90%甲醇/10%水(补给泵)
溶剂A:含有0.05%三氟乙酸的水
溶剂B:含有0.05%三氟乙酸的乙腈
制备实例
表A(下文)中的另外的化合物是通过类似程序从适当的起始材料制备。技术人员将理解,具有式(I)的化合物可以如上文所述的作为农艺学上可接受的盐、两性离子或农艺学上可接受的两性离子盐存在。在提及的情况下,不认为具体的抗衡离子是限制性的,并且具有式(I)的化合物可以用任何合适的抗衡离子形成。
除非另有说明,本文包含的NMR光谱在配备有Bruker SMART探针的400MHz BrukerAVANCE III HD上记录。化学位移表示为相对于TMS的低场ppm,其中TMS或残余溶剂信号为内部参考。以下多重性用于描述峰:s=单峰,d=二重峰,t=三重峰,dd=双二重峰,dt=双三重峰,q=四重峰,quin=五重峰,m=多重峰。另外br.用于描述宽的信号并且app.用于描述表观多重性。
实例1:2-[4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]乙磺酸酯A1的制备
步骤1:哒嗪-4-甲酸甲酯的制备
在0℃下,在氮气氛下,向哒嗪-4-甲酸(200mg)在甲醇(2mL)中的溶液中逐滴添加亚硫酰氯(0.49mL)。将反应混合物在65℃下搅拌2小时。将反应混合物浓缩并在乙酸乙酯(100mL)与碳酸氢钠饱和水溶液(50mL)之间分配。将水溶液用另外的乙酸乙酯(2x100mL)萃取。将合并的有机层浓缩以获得呈浅棕色固体的哒嗪-4-甲酸甲酯。
1H NMR(400MHz,DMSO-d6)9.58-9.60(m,1H)9.51-9.53(m,1H)8.11(dd,1H)3.93(s,3H)
步骤2:N-甲基哒嗪-4-甲酰胺的制备
将哒嗪-4-甲酸酯(50mg)在甲胺溶液(2M在甲醇中,1mL)中的混合物在密封容器中在100℃下加热2小时。将反应混合物冷却,浓缩并通过二氧化硅色谱法纯化(用己烷中的80%乙酸乙酯洗脱),得到呈棕色固体的N-甲基哒嗪-4-甲酰胺。
1H NMR(400MHz,DMSO-d6)9.51-9.53(m,1H)9.41-9.43(m,1H)8.97(brs,1H)7.96-7.98(m,1H)2.83(d,3H)
步骤3:2-[4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]乙磺酸酯A1的制备
向N-甲基哒嗪-4-甲酰胺(200mg)在水(4mL)中的混合物中添加2-溴乙磺酸钠(0.461g)。将混合物在100℃下加热30小时。将反应混合物浓缩并且用叔丁基甲基醚研制,以得到粗产物固体。将此粗产物固体通过制备型反相HPLC纯化,以得到呈白色固体的2-[4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]乙磺酸酯。
1H NMR(400MHz,D2O)9.88(d,1H),9.68(d,1H),8.74(d,1H),5.20-5.25(m,2H),3.55-3.66(m,2H),2.91(s,3H)(缺失NH质子)
实例2:3-[4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸三氟乙酸盐A4的制备
向N-甲基哒嗪-4-甲酰胺(200mg)在水(4mL)中的混合物中添加3-溴丙酸(0.401g)。将混合物在110℃下加热18小时,然后冷却并且浓缩。将粗产物用叔丁基甲基醚洗涤,并且将所得的粗产物通过制备型反相HPLC纯化以得到呈白色固体的3-[4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸三氟乙酸盐。
1H NMR(400MHz,D2O)9.94(d,1H),9.72(d,1H),8.80(dd,1H),5.16(t,2H),3.25(t,2H),2.98(s,3H)(缺失NH和CO2H质子)
实例3:3-[3-甲基-4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸2,2,2-三氟乙酸盐A57的制备
步骤1:3-甲基哒嗪-4-甲酸(2,3,4,5,6-五氟苯基)酯的制备
在室温下,在氮气氛下,向3-甲基哒嗪-4-甲酸(500mg)在二氯甲烷(5mL)中的溶液中逐滴添加4-二甲基氨基吡啶(89mg)和五氟苯酚(0.37mL)。将反应混合物在室温下搅拌16小时,然后用冰水淬灭(50mL)并且用乙酸乙酯(3x100mL)萃取。将合并的有机层浓缩以得到呈浅白色固体的3-甲基哒嗪-4-甲酸(2,3,4,5,6-五氟苯基)酯,其不经进一步纯化就可使用。
步骤2:N,3-二甲基哒嗪-4-甲酰胺的制备
在氮气氛下,将3-甲基哒嗪-4-甲酸(2,3,4,5,6-五氟苯基)酯(800mg)和甲胺溶液(4M在THF中,3.3mL)的混合物在80℃下加热16小时。将反应混合物冷却,浓缩并通过二氧化硅色谱法纯化(用己烷中的45%乙酸乙酯洗脱),得到呈棕色油状物的N,3-二甲基哒嗪-4-甲酰胺。
1H NMR(400MHz,DMSO-d6)9.19(d,1H)8.72(br s,1H)7.57(d,1H)2.79(d,3H)2.65(s,3H)
步骤3:3-[3-甲基-4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸乙酯溴化物的制备
向N,3-二甲基哒嗪-4-甲酰胺(300mg)在乙腈(6mL)中的溶液中添加3-溴丙酸乙酯(0.381mL)。将混合物在90℃下加热16小时,然后冷却并且浓缩。将粗产物用叔丁基甲基醚研制以得到呈黄色胶状物的粗产物3-[3-甲基-4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸乙酯溴化物,其不经进一步纯化就可用于下一步骤。
步骤4:3-[3-甲基-4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸2,2,2-三氟乙酸盐A57的制备
将粗产物3-[3-甲基-4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸乙酯溴化物(0.3g)在2M盐酸水溶液(10mL)中的溶液在室温下搅拌16小时。将反应混合物浓缩并通过制备型反相HPLC纯化(洗脱液中存在三氟乙酸)以得到3-[3-甲基-4-(甲基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸2,2,2-三氟乙酸盐。
1H NMR(400MHz,D2O)9.68(d,1H)8.42(d,1H)5.01(t,2H),3.18(t,2H),2.90(s,3H),2.73(s,3H)(缺失NH和CO2H质子)
实例4:3-[4-[甲基(苯基)氨基甲酰基]哒嗪-1-鎓-1-基]丙酸三氟乙酸盐A38的制备
步骤1:N-甲基-N-苯基-哒嗪-4-甲酰胺的制备
在室温下,在氮气氛下,向哒嗪-4-甲酸(1.5g)在N,N-二甲基甲酰胺(30mL)中的溶液中逐滴添加1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑[4,5-b]吡啶鎓3-氧化物六氟磷酸盐(5.20g),接着添加N,N-二异丙基乙胺(9.4g)。在30分钟搅拌之后,添加N-甲基苯胺(1.9g),并且再继续搅拌16小时。将反应混合物用水(50mL)淬灭并用乙酸乙酯(3x100mL)萃取。将有机相合并,用饱和氯化锂水溶液(2x100ml)洗涤并浓缩。将粗产物通过二氧化硅色谱法纯化(用己烷中的45%乙酸乙酯洗脱),得到呈棕色油状物的N-甲基-N-苯基-哒嗪-4-甲酰胺。
1H NMR(400MHz,DMSO-d6)9.13(br d,1H)9.08-8.95(m,1H)7.48(br s,1H)7.35-7.20(m,5H)2.68(s,3H)
步骤2:3-[4-[甲基(苯基)氨基甲酰基]哒嗪-1-鎓-1-基]丙酸甲酯溴化物的制备
向N-甲基-N-苯基-哒嗪-4-甲酰胺(800mg)在乙腈(16mL)中的溶液中添加3-溴丙酸甲酯(0.939g)。将混合物在90℃下加热18小时,然后浓缩并用叔丁基甲基醚洗涤,得到呈黄色胶状物的粗产物3-[4-[甲基(苯基)氨基甲酰基]哒嗪-1-鎓-1-基]丙酸甲酯溴化物,其不经进一步纯化就可使用。
步骤3:3-[4-[甲基(苯基)氨基甲酰基]哒嗪-1-鎓-1-基]2,2,2-三氟乙酸盐A38的制备
将粗产物3-[4-[甲基(苯基)氨基甲酰基]哒嗪-1-鎓-1-基]丙酸甲酯溴化物(0.6g)在2M盐酸水溶液(10mL)中的溶液在室温下搅拌16小时。将反应混合物浓缩并通过制备型反相HPLC纯化(洗脱液中存在三氟乙酸)以得到呈固体的3-[4-[甲基(苯基)氨基甲酰基]哒嗪-1-鎓-1-基]丙酸三氟乙酸盐。
1H NMR(400MHz,D2O)9.57(dd,1H),9.19(s,1H),8.32(dd,1H),7.22-7.35(m,5H),4.73-4.95(t,2H),3.45(s,3H),3.06(t,2H)(缺失CO2H质子)
实例5:3-[4-(哌啶-1-羰基)哒嗪-1-鎓-1-基]丙酸三氟乙酸盐A24的制备
步骤1:1-哌啶基(哒嗪-4-基)甲酮的制备
在室温下,在氮气氛下,向哒嗪-4-甲酸(0.6g)在乙腈(25mL)中的溶液中添加三乙胺(2.04mL)、丙基膦酸酐(6.15g)和哌啶(0.52mL)。将反应混合物在室温下搅拌16小时,然后浓缩,用水(50mL)稀释并用乙酸乙酯(3x100mL)萃取。将合并的有机层浓缩并通过二氧化硅色谱法纯化(用己烷中的45%乙酸乙酯洗脱),得到呈白色固体的1-哌啶基(哒嗪-4-基)甲酮。
1H NMR(400MHz,D2O)9.33(dd,1H)9.26(dd,1H)7.71(dd,1H)3.63-3.57(m,2H)3.24-3.18(m,2H)1.66-1.44(m,6H)
步骤2:3-[4-[甲基(苯基)氨基甲酰基]哒嗪-1-鎓-1-基]丙酸甲酯的制备
向1-哌啶基(哒嗪-4-基)甲酮(300mg)在乙腈(6mL)中的溶液中添加3-溴丙酸甲酯(0.324g)。将混合物在90℃下加热18小时,然后冷却并且浓缩。将粗产物用叔丁基甲基醚(50mL)洗涤以得到呈黄色胶状物的粗产物3-[4-[甲基(苯基)氨基甲酰基]哒嗪-1-鎓-1-基]丙酸甲酯溴化物,其不经进一步纯化就可使用。
步骤3:3-[4-(哌啶-1-羰基)哒嗪-1-鎓-1-基]丙酸三氟乙酸盐A24的制备
将粗产物3-[4-[甲基(苯基)氨基甲酰基]哒嗪-1-鎓-1-基]丙酸甲酯溴化物(485mg)在2M盐酸水溶液(10mL)中的溶液在室温下搅拌24小时。将反应混合物浓缩并通过制备型反相HPLC纯化(洗脱液中存在三氟乙酸)以得到3-[4-(哌啶-1-羰基)哒嗪-1-鎓-1-基]丙酸三氟乙酸盐。
1H NMR(400MHz,D2O)9.68-10.04(m,1H),9.32-9.64(m,1H),8.39-8.75(m,1H),5.00-5.22(m,2H),3.56-375(m,2H),3.28-3.34(m,2H),3.18-3.25(m,2H),1.63-1.73(m,4H),1.44-1.61(m,2H)(缺失CO2H质子)
实例6:2-[4-[(2-羟基苯基)氨基甲酰基]哒嗪-1-鎓-1-基]乙磺酸酯A84的制备
步骤1:2-哒嗪-4-基-1,3-苯并噁唑的制备
将2-氨基苯酚(0.19mL)、哒嗪-4-甲醛(250mg)、活性炭(194mg)和邻二甲苯(10mL)的混合物在120℃下加热过夜。将反应混合物通过硅藻土过滤,浓缩并通过制备型反相HPLC(洗脱液中存在三氟乙酸)纯化,得到呈米色固体的2-哒嗪-4-基-1,3-苯并噁唑。
1H NMR(400MHz,CD3OD)9.93(dd,1H),9.45(dd,1H),8.40(dd,1H),7.89-7.84(m,1H),7.78(dd,1H),7.57-7.46(m,2H)
步骤2:2-[4-[(2-羟基苯基)氨基甲酰基]哒嗪-1-鎓-1-基]乙磺酸酯A84的制备
将2-哒嗪-4-基-1,3-苯并噁唑(100mg)、2-溴乙烷磺酸(131mg)和水(2mL)的混合物在100℃下加热20小时。添加另外的2-溴乙烷磺酸(131mg)并且再继续加热6小时。将反应混合物浓缩并通过制备型反相HPLC(洗脱液中存在三氟乙酸)纯化,得到呈橙色固体的2-[4-[(2-羟基苯基)氨基甲酰基]哒嗪-1-鎓-1-基]乙磺酸酯。
1H NMR(400MHz,DMSO-d6)10.60(s,1H),10.11(d,1H),9.99-9.83(m,2H),9.00(dd,1H),7.65(br d,1H),7.16-7.07(m,1H),6.96(d,1H),6.87(t,1H),5.13(br t,2H),3.27-3.20(m,2H)
实例7:[(1S)-1-羧基-2-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基)乙基]铵2,2,2-三氟乙酸盐A121的制备
步骤1:(2S)-2-(叔丁氧基羰基氨基)-3-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸2,2,2-三氟乙酸盐的制备
在室温下,在氮气氛下,向N-乙基哒嗪-4-甲酰胺(0.3g)在干燥乙腈(6mL)中的溶液中添加N-[(3S)-2-氧代氧杂环丁烷-3-基]氨基甲酸叔丁酯(0.668g)。在完成之后,将反应混合物浓缩并使用制备型反相HPLC纯化(洗脱液中存在三氟乙酸),得到粗产物(2S)-2-(叔丁氧基羰基氨基)-3-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸2,2,2-三氟乙酸盐,其不经进一步纯化就可用于下一步骤。
LCMS:保留时间0.29min,M+339
步骤2:[(1S)-1-羧基-2-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基)乙基]铵2,2,2-三氟乙酸盐A121的制备
将(2S)-2-(叔丁氧基羰基氨基)-3-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基]丙酸2,2,2-三氟乙酸盐(0.06g)和2M盐酸水溶液(4mL)的混合物在室温下搅拌24小时。将反应混合物真空浓缩并通过制备型反相HPLC(洗脱液中存在三氟乙酸)纯化,得到[(1S)-1-羧基-2-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基)乙基]铵;2,2,2-三氟乙酸盐。
1H NMR(400MHz,D2O)10.00(d,1H),9.80(d,1H),8.90-8.93(m,1H),5.49(d,2H),4.64(t,1H),3.46-3.52(m,2H),1.25(t,3H)。(缺失NH和CO2H质子)
实例8:[(1S)-1-羧基-3-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基)丙基]二氯化铵A91的制备
步骤1:[(1S)-3-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基]-1甲氧基羰基-丙基]铵2,2,2-三氟乙酸盐A93的制备
在室温下,在氮气氛下,向N-乙基哒嗪-4-甲酰胺(0.3g)在干燥乙腈(6mL)中的溶液中添加[(1S)-3-溴-1-甲氧基羰基丙基]氯化铵(0.55g,制备如WO2019/034757中所述)。将反应混合物在回流下加热16小时,浓缩并通过制备型反相HPLC纯化(洗脱液中存在三氟乙酸),得到呈胶状物的[(1S)-3-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基]-1甲氧基羰基-丙基]铵2,2,2-三氟乙酸盐。
1H NMR(400MHz,D2O)9.92(d,1H),9.74(dd,1H),8.83(dd,1H),5.16(t,2H),4.33(dd,1H),3.83(s,3H),3.44(q,2H),2.78-2.83(m,1H),2.66-2.76(m,1H),1.20(t,3H)(缺失NH质子)
步骤2:[(1S)-1-羧基-3-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基)丙基]二氯化铵A91的制备
将(2S)-2-氨基-4-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基]丁酸甲酯2,2,2-三氟乙酸盐(0.05g)在2M盐酸水溶液(1mL)中的混合物在60℃下加热12小时。将反应混合物浓缩,得到呈胶状物的[(1S)-1-羧基-3-[4-(乙基氨基甲酰基)哒嗪-1-鎓-1-基)丙基]二氯化铵。
1H NMR(400MHz,D2O)9.94(d,1H),9.75(d,1H),8.83(dd,1H),5.18(t,2H),4.11-4.18(m,1H),3.46(q,2H),2.68-2.84(m,2H),1.21(t,3H)(缺失NH和CO2H质子)
实例9:3-[4-[2-(5,5-二甲基-4H-异噁唑-3-基)乙基氨基甲酰基]哒嗪-1-鎓-1-基]丙酸2,2,2-三氟乙酸盐A148的制备
步骤1:N-(3-氧代丙基)氨基甲酸叔丁酯的制备
在0℃下,在氮气氛下,向3-(Boc-氨基)-1-丙醇(5g)在二氯甲烷(150mL)中的溶液中添加戴斯-马丁氧化剂(14.08g)。将反应混合物加温至室温并搅拌2小时。将反应混合物用水(120mL)稀释并用二氯甲烷(3x70mL)萃取。将合并的有机层用1M硫代硫酸钠水溶液和饱和碳酸氢钠洗涤,经硫酸钠干燥并浓缩,得到呈棕色胶状物的N-(3-氧代丙基)氨基甲酸叔丁酯,其不经进一步纯化就可用于下一步骤。
步骤2:N-(3-羟基亚氨基丙基)氨基甲酸叔丁酯的制备
向N-(3-氧代丙基)氨基甲酸叔丁酯(5g)在乙醇(100mL)中的溶液中添加盐酸羟胺(2.82g)和碳酸钠(8.26g),并且将所得混合物在室温下搅拌16小时。将反应混合物用水(120mL)稀释并用乙酸乙酯(3x100mL)萃取。将合并的有机层用水、盐水洗涤,经硫酸钠干燥并浓缩,得到呈棕色固体的N-(3-羟基亚氨基丙基)氨基甲酸叔丁酯,其不经进一步纯化就可用于下一步骤。
步骤3:N-[2-(5,5-二甲基-4H-异噁唑-3-基)乙基]氨基甲酸叔丁酯的制备
在室温下,向N-(3-羟基亚氨基丙基)氨基甲酸叔丁酯(4.5g)在N,N-二甲基甲酰胺(45ml)中的溶液中分批添加N-氯代丁二酰亚胺(3.95g)。在搅拌2小时之后,添加碳酸钾(4g),并且将反应混合物冷却至-40℃。在-40℃下,向混合物中吹入异丁烯气体(约14g),持续30分钟,并且然后在室温下搅拌4小时。将反应物缓慢加温至室温并搅拌18小时。将反应物用冰水淬灭并用乙酸乙酯萃取(3x50mL)。将合并的有机层用盐水洗涤,经无水硫酸钠干燥,浓缩并通过硅胶柱色谱法纯化(用乙酸乙酯在异己烷中的混合物洗脱),得到呈灰白色固体的N-[2-(5,5-二甲基-4H-异噁唑-3-基)乙基]氨基甲酸叔丁酯。
1H NMR(400MHz,CDCl3)4.95(br s,1H),3.40(br d,2H),2.70(s,2H),2.46(t,2H),1.42(s,9H),1.37(s,6H)
步骤4:2-(5,5-二甲基-4H-异噁唑-3-基)乙基铵2,2,2-三氟乙酸盐的制备。
在0℃下,向N-[2-(5,5-二甲基-4H-异噁唑-3-基)乙基]氨基甲酸叔丁酯(1g)在二氯甲烷(20mL)中的溶液中添加2,2,2-三氟乙酸(2.87mL)。将反应物加温至室温并搅拌18小时。将反应物质浓缩,并且将所得残余物用叔丁基甲基醚(2x20mL)洗涤并在减压下干燥,得到呈灰白色固体的2-(5,5-二甲基-4H-异噁唑-3-基)乙基铵2,2,2-三氟乙酸盐。
1H NMR(400MHz,DMSO-d6)7.88(br s,3H),3.00-3.09(m,2H),2.76(s,2H),2.57(t,2H),1.29(s,6H)
步骤5:N-[2-(5,5-二甲基-4H-异噁唑-3-基)乙基]哒嗪-4-甲酰胺的制备。
在室温下,向哒嗪-4-甲酸(2,3,4,5,6-五氟苯基)酯(0.5g)在乙腈(10mL)中的溶液中添加2-(5,5-二甲基-4H-异噁唑-3-基)乙基铵2,2,2-三氟乙酸盐(0.48g)和碳酸钾(0.6g)。使反应物质在100℃下经受微波辐射1小时。将反应物浓缩并通过硅胶柱色谱法纯化(用甲醇在二氯甲烷中的混合物洗脱),得到N-[2-(5,5-二甲基-4H-异噁唑-3-基)乙基]哒嗪-4-甲酰胺。
1H NMR(400MHz,CD3OD)9.49(dd,1H),9.37(dd,1H),8.00(dd,1H),3.67(t,2H),2.88(s,2H),2.65(t,2H),1.35(s,6H)(缺失NH质子)
步骤6:3-[4-[2-(5,5-二甲基-4H-异噁唑-3-基)乙基氨基甲酰基]哒嗪-1-鎓-1-基]丙酸2,2,2-三氟乙酸盐A148的制备
向N-[2-(5,5-二甲基-4H-异噁唑-3-基)乙基]哒嗪-4-甲酰胺(0.25g)在乙腈(5mL)中的溶液中添加3-溴丙酸(0.32g),并且将混合物在80℃下加热18小时。将反应物冷却,浓缩并通过制备型反相HPLC纯化(洗脱液中存在三氟乙酸),得到呈灰白色固体的3-[4-[2-(5,5-二甲基-4H-异噁唑-3-基)乙基氨基甲酰基]哒嗪-1-鎓-1-基]丙酸2,2,2-三氟乙酸盐。
1H NMR(400MHz,D2O)9.94(d,1H),9.68(d,1H),8.76(dd,1H),5.15(t,2H),3.67(t,2H),3.26(t,2H),2.93(s,2H),2.67(t,2H),1.32(s,6H)(缺失NH和CO2H质子)
对于化合物A131,胺的合成可以见于WO 16071359。
表A-本发明的化合物的物理数据
生物学实例
出苗后功效
将多种测试物种的种子播种在盆中的标准土壤中。在温室中的受控条件(24℃/16℃,昼/夜;14小时光照;65%湿度)下培养14天后(出苗后),用如下得到的水性喷雾溶液喷洒植物:将具有式(I)的技术活性成分在少量丙酮和称为IF50(11.12%Emulsogen EL360TM+44.44%N-甲基吡咯烷酮+44.44%Dowanol DPM乙二醇醚)的特殊溶剂和乳化剂混合物中溶解,以制备50g/l溶液,然后使用0.25%或1%Empicol ESC70(月桂基醚硫酸钠)+1%硫酸铵作为稀释剂将其稀释至所需浓度。
然后使测试植物在受控条件(24℃/16℃,昼/夜下;14小时光照;65%湿度)下生长于温室中,并且每天浇水两次。13天后,评估测试(100=对植物的完全损害;0=无植物损害)。
结果示于表B(下文)中。n/a值指示未测试/评估此杂草和测试化合物组合。
测试植物:
牵牛花(IPOHE)、白苞猩猩草(EPHHL)、藜草(CHEAL)、长芒苋(AMAPA)、多年生黑麦草(LOLPE)、马唐(DIGSA)、牛筋草(ELEIN)、稗草(ECHCG)、大狗尾草(SETFA)
表B-通过出苗后施用具有式(I)的化合物对杂草物种的控制
Claims (16)
1.具有式(I)的化合物或其农艺学上可接受的盐或两性离子物种作为除草剂的用途:
其中,
R1选自由以下各项组成的组:氢、卤素、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、-OR7、-OR15a、-N(R6)S(O)2R15、-N(R6)C(O)R15、-N(R6)C(O)OR15、–N(R6)C(O)NR16R17、-N(R6)CHO、-N(R7a)2和-S(O)rR15;
R2选自由以下各项组成的组:氢、卤素、C1-C6烷基和C1-C6卤代烷基;
并且其中当R1选自由–OR7、-OR15a、-N(R6)S(O)2R15、-N(R6)C(O)R15、-N(R6)C(O)OR15、–N(R6)C(O)NR16R17、-N(R6)CHO、-N(R7a)2和-S(O)rR15组成的组时,R2选自由氢和C1-C6烷基组成的组;或者
R1和R2与它们所附接的碳原子一起形成C3-C6环烷基环或3元至6元杂环基,其包含1或2个单独地选自N和O的杂原子;并且
Q是(CR1aR2b)m;
m是0、1、2或3;
每个R1a和R2b独立地选自由以下各项组成的组:氢、卤素、C1-C6烷基、C1-C6卤代烷基、-OH、-OR7、-OR15a、-NH2、-NHR7、-NHR15a、-N(R6)CHO、-NR7bR7c以及–S(O)rR15;或者
每个R1a和R2b与它们所附接的碳原子一起形成C3-C6环烷基环或3元至6元杂环基,其包含1或2个单独地选自N和O的杂原子;并且
R3、R4和R5独立地选自由以下各项组成的组:氢、氰基、硝基、C1-C6烷基、C1-C6硫代烷基、C1-C6氟烷基、C1-C6氟烷氧基、C1-C6烷氧基、C3-C6环烷基、苯基和-N(R6)2;
每个R6独立地选自氢和C1-C6烷基;
每个R7独立地选自由以下各项组成的组:C1-C6烷基、-S(O)2R15、-C(O)R15、-C(O)OR15以及-C(O)NR16R17;
每个R7a独立地选自由以下各项组成的组:-S(O)2R15、-C(O)R15、-C(O)OR15、-C(O)NR16R17和-C(O)NR6R15a;
R7b和R7c独立地选自由以下各项组成的组:C1-C6烷基、-S(O)2R15、-C(O)R15、-C(O)OR15、-C(O)NR16R17和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;或者
R7b和R7c与它们所附接的氮原子一起形成4元至6元杂环基环,其任选地包含一个另外的单独地选自N、O和S的杂原子;并且
R8a选自由以下各项组成的组:氢、-OH、-OR7、-S(O)rR15、-C(O)OR10、-C(O)R15、-C(O)NR16R17、-S(O)2NR16R17、-NR7dR7e、R15S(O)rC1-C3烷基-、R16R17NS(O)2C1-C3烷基-、R15C(O)C1-C3烷基-、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷氧基、C3-C6环烷基C1-C3烷基-、C3-C6环烷基C1-C3烷氧基-、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、C1-C3烷氧基C1-C3烷氧基-、C1-C6卤代烷氧基、C1-C3卤代烷氧基C1-C3烷基-、C3-C6烯基氧基、C3-C6炔基氧基、-C(R6)=NOR6、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中所述杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中所述杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1、2或3个可以是相同或不同的R9取代基取代;
R8b选自由以下各项组成的组:氢、-OR7、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C3-C6环烷氧基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、C1-C3烷氧基C1-C3烷氧基-、C1-C6卤代烷氧基、C1-C3卤代烷氧基C1-C3烷基-、C3-C6烯基氧基以及C3-C6炔基氧基;或者
R8a和R8b与它们所附接的氮原子一起形成4元至6元杂环基,其任选地包含1或2个另外的独立地选自N、O和S(O)r的杂原子,并且其中所述杂环基部分任选地被1或2个可以是相同或不同的R9取代基取代;并且
R7d和R7e独立地选自由以下各项组成的组:氢、C1-C6烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C1-C3烷氧基C1-C3烷基-、C2-C6炔基、-S(O)2R15、-C(O)R15、-C(O)OR15、-C(O)NR16R17和苯基,并且其中所述苯基任选地被1、2或3个R9取代基取代;
每个R9独立地选自由以下各项组成的组:-OH、卤素、氰基、-N(R6)2、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基;
X选自由以下各项组成的组:C3-C6环烷基、苯基、包含1、2、3或4个单独地选自N、O和S的杂原子的5元或6元杂芳基、和包含1、2或3个单独地选自N、O和S的杂原子的4元至6元杂环基,并且其中所述环烷基、苯基、杂芳基或杂环基部分任选地被1或2个R9取代基取代,并且其中所述前述CR1R2、Q和Z部分可以附接在所述环烷基、苯基、杂芳基或杂环基部分的任何位置;
n是0或1;
Z选自由以下各项组成的组:-C(O)OR10、-CH2OH、-CHO、-C(O)NHOR11、-C(O)NHCN、-OC(O)NHOR11、-OC(O)NHCN、-NR6C(O)NHOR11、-NR6C(O)NHCN、-C(O)NHS(O)2R12、-OC(O)NHS(O)2R12、-NR6C(O)NHS(O)2R12、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10、-NR6S(O)OR10、-NHS(O)2R14、-S(O)OR10、-OS(O)OR10、-S(O)2NHCN、-S(O)2NHC(O)R18、-S(O)2NHS(O)2R12、-OS(O)2NHCN、-OS(O)2NHS(O)2R12、-OS(O)2NHC(O)R18、-NR6S(O)2NHCN、-NR6S(O)2NHC(O)R18、-N(OH)C(O)R15、-ONHC(O)R15、-NR6S(O)2NHS(O)2R12、-P(O)(R13)(OR10)、-P(O)H(OR10)、-OP(O)(R13)(OR10)、-NR6P(O)(R13)(OR10)和四唑;
R10选自由以下各项组成的组:氢、C1-C6烷基、苯基和苄基,并且其中所述苯基或苄基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R11选自由以下各项组成的组:氢、C1-C6烷基和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R12选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、-OH、-N(R6)2和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R13选自由以下各项组成的组:-OH、C1-C6烷基、C1-C6烷氧基和苯基;
R14是C1-C6卤代烷基;
R15选自由以下各项组成的组:C1-C6烷基和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R15a是苯基,其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
R16和R17独立地选自由以下各项组成的组:氢和C1-C6烷基;或者
R16和R17与它们所附接的氮原子一起形成4元至6元杂环基环,其任选地包含一个另外的独立地选自N、O和S的杂原子;并且
R18选自由以下各项组成的组:氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、-N(R6)2和苯基,并且其中所述苯基任选地被1、2或3个可以是相同或不同的R9取代基取代;
并且
r是0、1或2。
3.根据权利要求1所述的具有式(I)的化合物或根据权利要求2所述的具有式(I)的化合物的用途,其中,R1和R2独立地选自由以下各项组成的组:氢和C1-C6烷基。
4.根据权利要求1至3中任一项所述的具有式(I)的化合物或根据权利要求2或权利要求3所述的具有式(I)的化合物的用途,其中,每个R1a和R2b独立地选自由以下各项组成的组:氢、C1-C6烷基、-OH和-NH2。
5.根据权利要求1至4中任一项所述的具有式(I)的化合物或根据权利要求2至4中任一项所述的具有式(I)的化合物的用途,其中,m是1或2。
6.根据权利要求1至5中任一项所述的具有式(I)的化合物或根据权利要求2至5中任一项所述的具有式(I)的化合物的用途,其中,R3、R4和R5独立地选自由以下各项组成的组:氢、C1-C6烷基和苯基。
7.根据权利要求1至6中任一项所述的具有式(I)的化合物或根据权利要求2至6中任一项所述的具有式(I)的化合物的用途,其中,R3、R4和R5是氢。
8.根据权利要求1至7中任一项所述的具有式(I)的化合物或根据权利要求2至7中任一项所述的具有式(I)的化合物的用途,其中,R8a选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6环烷基C1-C3烷基-、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、羟基C1-C6烷基-、氰基C1-C6烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基和杂芳基C1-C2烷基-,其中所述杂环基部分是包含1、2或3个单独地选自N、O和S(O)r的杂原子的4元至6元饱和或部分饱和的环,其中所述杂芳基是包含1、2、3或4个独立地选自N、O和S的杂原子的5元或6元芳香族环,并且其中所述C3-C6环烷基、C3-C6环烷基C1-C3烷基-、苯基、苯基C1-C2烷基-、杂环基、杂环基C1-C2烷基-、杂芳基或杂芳基C1-C2烷基-任选地被1个R9取代基取代。
9.根据权利要求1至8中任一项所述的具有式(I)的化合物或根据权利要求2至8中任一项所述的具有式(I)的化合物的用途,其中,R8a选自由以下各项组成的组:C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6炔基、C1-C3烷氧基C1-C3烷基-、氰基C1-C3烷基-、苯基和杂环基,其中所述杂环基部分是包含1个S(O)r杂原子的4元至6元饱和或部分饱和的环,并且其中所述苯基任选地被1个R9取代基取代。
10.根据权利要求1至9中任一项所述的具有式(I)的化合物或根据权利要求2至9中任一项所述的具有式(I)的化合物的用途,其中,R8b选自由以下各项组成的组:氢、C1-C6烷基和C2-C3炔基。
11.根据权利要求1至7中任一项所述的具有式(I)的化合物或根据权利要求2至7中任一项所述的具有式(I)的化合物的用途,其中,R8a和R8b与它们所附接的氮原子一起形成5元至6元杂环基,其任选地包含1个另外的O杂原子。
12.根据权利要求1至11中任一项所述的具有式(I)的化合物或根据权利要求2至11中任一项所述的具有式(I)的化合物的用途,其中,Z选自由以下各项组成的组:-C(O)OR10、-S(O)2OR10、-OS(O)2OR10、-NR6S(O)2OR10和-NHS(O)2R14。
13.根据权利要求1至12中任一项所述的具有式(I)的化合物或根据权利要求2至12中任一项所述的具有式(I)的化合物的用途,其中,Z是-C(O)OH或-S(O)2OH。
14.根据权利要求1至13中任一项所述的具有式(I)的化合物或根据权利要求2至13中任一项所述的具有式(I)的化合物的用途,其中,n是0。
15.一种农用化学组合物,其包含除草有效量的如权利要求1至14中任一项所定义的具有式(I)的化合物、以及农用化学上可接受的稀释剂或载体。
16.一种控制不想要的植物生长的方法,其包括将如权利要求1至14中任一项所定义的具有式(I)的化合物或根据权利要求15所述的除草组合物施用至所述不想要的植物或施用至其场所。
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