CN87105345A - 叔胺化合物 - Google Patents
叔胺化合物 Download PDFInfo
- Publication number
- CN87105345A CN87105345A CN198787105345A CN87105345A CN87105345A CN 87105345 A CN87105345 A CN 87105345A CN 198787105345 A CN198787105345 A CN 198787105345A CN 87105345 A CN87105345 A CN 87105345A CN 87105345 A CN87105345 A CN 87105345A
- Authority
- CN
- China
- Prior art keywords
- compound
- alkyl
- group
- phenyl
- water
- 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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- -1 Tertiary amine compound Chemical class 0.000 title claims description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 94
- 238000002360 preparation method Methods 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 10
- 230000000855 fungicidal effect Effects 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000003053 piperidines Chemical class 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 230000000843 anti-fungal effect Effects 0.000 claims 1
- 230000002508 compound effect Effects 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 157
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 60
- 238000001035 drying Methods 0.000 description 45
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
- 239000002585 base Substances 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
- 238000005406 washing Methods 0.000 description 31
- 239000012074 organic phase Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 20
- 238000007738 vacuum evaporation Methods 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000945 filler Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 230000005526 G1 to G0 transition Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 229910052710 silicon Inorganic materials 0.000 description 12
- 239000010703 silicon Substances 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 230000033228 biological regulation Effects 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 241000233866 Fungi Species 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 238000003810 ethyl acetate extraction Methods 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 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 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 229910052727 yttrium Inorganic materials 0.000 description 5
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- 235000011430 Malus pumila Nutrition 0.000 description 4
- 244000070406 Malus silvestris Species 0.000 description 4
- 235000015103 Malus silvestris Nutrition 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- IZZWJPQHPPRVLP-UHFFFAOYSA-N hexane;2-methoxy-2-methylpropane Chemical compound CCCCCC.COC(C)(C)C IZZWJPQHPPRVLP-UHFFFAOYSA-N 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 4
- 239000012053 oil suspension Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 230000001717 pathogenic effect Effects 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 230000008635 plant growth Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
- KLBIUKJOZFWCLW-UHFFFAOYSA-N thallium(iii) nitrate Chemical compound [Tl+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O KLBIUKJOZFWCLW-UHFFFAOYSA-N 0.000 description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 241001674391 Sphaerulina musiva Species 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229940125846 compound 25 Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- NAKRHRXBVSLQAO-UHFFFAOYSA-N diethyl cyclopentane-1,1-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CCCC1 NAKRHRXBVSLQAO-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000006197 hydroboration reaction Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229940031815 mycocide Drugs 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000024241 parasitism Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000005554 pickling Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 229960004249 sodium acetate Drugs 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
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Abstract
具有抗植物真菌性质的通式(I)的化合物及其立体异构体,其中R1和R2各自代表氢原子、卤原子或者含有1-4个碳原子的烷基,R3和R4各自代表氢或含1-4个碳原子的烷基,R5和R6各自代表含1-4个碳原子的烷基,或者与邻近的氮原子一起形成杂环;环中有时还包含一个其它杂原子,X和Y各自代表氢原子、卤原子或者烷基、环烷基、环烷基烷基、链烯基、炔基、芳基、芳烷基、烷氧基或芳氧基,n的值为0或1,Q和Z是桥连基团。
Description
本发明涉及含有环丁烷、环戊烷或环己烷环的、可用作杀真菌剂的叔胺化合物,涉及该类化合物的制备方法、含有该类化合物的杀真菌组合物以及用其杀灭真菌、尤其是植物上的真菌感染的方法。
本发明提供具有如下通式(Ⅰ)的化合物、它们的立体异构体及酸加成盐:
其中R1和R2各代表氢原子,卤素原子,或C1-4烷基,R3和R4各代表氢原子或C1-4烷基,R5和R6各代表C1-4烷基或R5和R6及相邻的氮原子一起形成一个杂环,杂环中可含有另一杂原子,X和Y各代表氢原子,卤原子,或烷基,环烷基,环烷基烷基,链烯基,炔基,芳基,芳烷基,烷氧基或芳氧基,或下式代表的基团,
其中R19、R20和R21可代表烷基,链烯基,炔基,环烷基,环烷基烷基,芳基或芳烷基,n为0或1,Q和Z是后面规定的桥基。
桥基Q具有下列Q1,Q2,Q3和Q4其中之一的结构(要受后面所述的条件限制):
其中R7到R14各自独立地代表氢原子,卤原子,羟基或C1-4烷基。
桥基Z可以是一个共价键(用Z0表示),或者可以是具有下列Z1和Z2其中之一的结构(要受后面所述的条件限制):
其中R15到R18各自独立地具有上述R7到R14的相同意义。确定桥基Q和Z的结构要受下列条件的限制:
(ⅰ)当Z为Z0时,Q不可为Q1;
(ⅱ)构成式(Ⅰ)中环结构的一部分、由Q和Z提供的碳原子总数不得大于4。
本发明的化合物一般是以其几何异构体的混合物形式制得。但这些混合物和其它旋光异构体混合物都可用该领域的方法分为各别异构体,而这些异构体也构成本发明的一部分。
当R5和R6与相邻的N原子一起代表一个杂环时,例如可以是哌啶,吗啉,硫代吗啉,吡咯烷或哌嗪环,这些环中任何一个都可带取代基,如一个或多个C1-4烷基或苯基,或一个羟烷基。
R1,R2,R3,R4和R7到R18所代表的C1-4烷基可以是直链或支链的基团,例如甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基。X和Y及R19到R21代表的烷基或烷氧基中的烷基可以是含1~6个碳原子的直链或带支链基团;X和Y及R19到R21代表的环烷基可以是C3-6环烷基,例如环丙基,环丁基,环戊基或环己基;或者环烷基烷基,例如C4-C9环烷基烷基。
R1和R2,R7到R18以及X和Y代表的卤原子可以是氟,氯或溴原子。
X和Y代表的链烯基和炔基可以含有2~6个碳原子,而R19到R21代表的这两种基团含有2~4个碳原子。
X和Y代表的芳基,芳烷基,芳氧基或芳烷氧基的例子有苯基,苄基,苯氧基和苄氧基。R19到R21代表的芳基或芳烷基的例子有苯基和苄基。这些环可以被卤素(如氟,氯,或溴),C1-6烷基〔如甲基,乙基,丙基(正或异丙基)和丁基(正,仲,异,或叔丁基)〕,C1-6烷氧基(如甲氧基,乙氧基,丙氧基和丁氧基),卤代C1-6烷氧基(如三氟甲氧基),卤代C1-6烷基(如三氟甲基),硝基,苯基和苯氧基取代。X和Y表示的甲硅烷基的例子有三甲基甲硅烷基,三乙基甲硅烷基,叔丁基二甲基甲硅烷基,苯基二甲基甲硅烷基和烯丙基二甲基甲硅烷基。苯环可以是非取代的或被上面限定的环上取代基取代。X和Y取代基可以在苯环的2,3或4位、最好在4位上取代。
根据本发明的一种具体情况,提供了含有环丁烷环并且具有下述通式(Ⅰ)的化合物及其立体异构体和酸加成盐,
其中,可以按前述规定使Q具有Q2的结构,Z具有Z0的结构,也可以按前述规定使Q具有Q1的结构,Z具有Z1的结构,其它符号的意义同前所述。这两种选择所对应的式(Ⅰ)化合物为:其分子的残余部分
分别连在环丁烷环的1,2位和1,3位。
根据本发明的另一种具体情况,提供了具有环戊烷环并且具有上述通式(Ⅰ)的化合物。如前规定Q具有Q3的结构而Z具有Z0的结构,或者Q具有Q3的结构而Z具有Z1的结构,其它的符号的意义同前所述。这两种可能性相应于上述的分子残余部分分别在环戊烷环的1,2位和1,3位上取代。
根据本发明的再一种具体情况,提供了含有环己烷环并具有上述通式(Ⅰ)的化合物,如前所述其中Q具有Q4的结构而Z具有Z0的结构,或者Q具有Q3的结构而Z具有Z1的结构,或者Q具有Q3的结构而Z具有Z3的结构,其它的符号意义同前。这三种可能性分别相应于上述的分子残余部分在环己烷环的1,2位,1,3位或1,4位取代。
本发明化合物的例子列于表Ⅰ到Ⅶ中。它们的通式(Ⅰ)中分别含有1,3-二取代的环丁烷,1,3-二取代的环戊烷,1,2-二取代的环丁烷,1,2-二取代的环戊烷,1,3-二取代的环己烷,1,2-二取代的环己烷和1,4-二取代的环己烷。
(见7页至31页图表)
通式(Ⅰ)的化合物的制备方法是在通常的溶剂如乙醚,四氢呋喃或二噁烷中,用还原剂(通常是氢化铝锂)处理通式(Ⅱ)的化合物,
其中R1到R6,Q,X,Y,Z和n的规定同上,R3=R4=氢,
其中R1,R2,R5,R6,Q,X,Y,Z和n的规定同上。
通式(Ⅱ)的酰胺的制备方法是在通常的溶剂(如乙醚或四氢呋喃)中,使通式(Ⅲ)的酰氯与通式(Ⅳ)的胺反应,
其中R1,R2,Q,X,Y,Z和n的规定同上,
其中R5和R6的规定同上。
通式(Ⅲ)的酰氯的制备方法是在方便的溶剂(如己烷或二氯甲烷)中,使通式(Ⅴ)的酸与通常的氯化试剂(如亚硫酰氯或草酰氯)反应,
其中R1,R2,Q,X,Y,Z和n的规定同上。
通式(Ⅴ)的酸的制备方法是按通常的方式,在甲醇/水溶液中,在20~60℃,用氢氧化钠或氢氧化钾使通式(Ⅵ)的酯水解,
(见下页)
其中R1,R2,Q,X,Y,Z和n的规定同上,R是烷基。
此外,通式(Ⅰ)中R4是氢的化合物的制备方法是在还原剂(如甲酸,氰基硼氢化钠或氰基硼氢化四丁基铵)存在下,用通式(Ⅳ)的胺处理通式(Ⅶ)的化合物:
其中R1到R3,Q,X,Y,Z和n的规定同上。
还可以用下述方法制备通式(Ⅰ)的化合物,即在方便的溶剂(如乙醇或四氢呋喃)中,或者最好不用溶剂,在20~100℃温度下,用通式(Ⅳ)的胺处理通式(Ⅷ)的化合物:
(式Ⅷ见下页)
其中R1到R4,Q,X,Y,Z和n的规定同上,W是离去基团,如氯,溴,甲磺酸根或甲苯磺酸根。
通式(Ⅷ)的化合物的制备方法是:用通常的卤化试剂(如当W=
氯时用三氯化磷、五氯化磷或氯氧化磷;当W=溴时用三溴化磷、五溴化磷或溴氧化磷),或者当W=甲磺酸根时用甲磺酰氯吡啶(或三乙胺)溶液,或者当W=甲苯磺酸根时用甲苯磺酰氯吡啶(或三乙胺)溶液,处理通式(Ⅸ)的醇:
其中R1到R4,Q,X,Y,Z和n的规定同上。
通式(Ⅶ)中R3=氢的酮的制备方法是:在-78℃下,在方便的溶剂中(如甲苯),用等当量的氢化二异丁基铝处理通式(Ⅵ)的酯。
通式(Ⅶ)的酮的另一种制备方法是:在低温(如-30℃)下,在方便的溶剂(如四氢呋喃)中,用通式(Ⅹ)的格利雅试剂处理通式(Ⅲ)的酰氯:
R3MgBr(Ⅹ)
其中R3的定义同上。
还有一种制备通式(Ⅶ)的酮的方法,即用通常的氧化剂,例如三氧化铬,氧化通式(Ⅸ)中R4=氢的醇,或者用Moffat氧化法的Swern改进方法(二甲亚砜,草酰氯,然后三乙胺)氧化上述通式(Ⅸ)化合物(R4为氢)。
还有一种制备通式(Ⅶ)的酮的方法,即用酸的水溶液,如稀盐酸,使通式(Ⅺ)的烯醇醚水解:
其中R,R1到R3,Q,X,Y,Z和n定义同上。
制备通式(Ⅺ)的稀醇醚的方法如文献所叙述,在方便的溶剂中,用通式(ⅩⅢ)的正膦,或用通式(ⅩⅣ)的氧化膦阴离子,处理通式(Ⅻ)的酮:
其中R1,R2,Q,X,Y,Z和n定义同上;
其中R和R3定义同上;
其中R和R3定义同上。
通式(Ⅸ)中R3=R4=氢的醇的制备方法是:在通常用的溶剂(如乙醚或四氢呋喃)中,用还原剂(通常是氢化铝锂)处理通式(Ⅵ)的酯。
此外,通式(Ⅸ)中R3=R4=烷基的醇的制备方法是:在一般的溶剂(如乙醚或四氢呋喃)中,用过量的通式(Ⅹ)的格利雅试剂,或用过量的烷基锂试剂处理通式(Ⅵ)的酯。
还有一种制备通式(Ⅸ)的醇的方法,即在一般的溶剂(如乙醚或四氢呋喃)中,用通式(ⅩⅤ)的格利雅试剂,或用烷基锂试剂处理通式(Ⅶ)的酮,
R4MgBr(ⅩⅤ)
其中R4的定义同上。
还有一种制备通式(Ⅸ)中R4=氢的醇的方法:即使通式(ⅩⅥ)的烯发生硼氢化反应,然后进行氧化处理,
其中R1到R3,Q,X,Y,Z和n的定义同上。
要制备通式(ⅩⅥ)的烯,可按文献中叙述的方法,在维悌希反应或其改良方法条件下,由相应的通式(Ⅻ)的酮与通式(ⅩⅦ)的正膦反应:
其中R3的定义同上。
通式(Ⅻ)中Q=Q1,(R7=R8=氢)且Z=Z1的酮可以这样制备:用还原剂如氢化三丁基锡或乙酸中的锌使通式(ⅩⅧ)的酮发生脱氯作用,
其中R1,R2,R15,R16,X,Y和n的定义同上(但R15和R16只代表氢原子或烷基)。
通式(ⅩⅧ)的酮可以这样制备:使通式(ⅩⅨ)的烯与二氯乙烯酮反应,
其中R1,R2,R15,R16,X,Y和n的定义如上段所规定。而二氯乙烯酮的制备方法例如是使锌作用于三氯乙酰氯或者使三乙胺作用于二氯乙酰氯。
通式(ⅩⅨ)的烯可以用文献中提出的方法制备。
此外,还可以按下述方法制备通式(ⅩⅡ)中Z=Z1,(R15=氢,R16=氢或烷基)以及Q=Q2或Q3的酮:使通式(ⅩⅩ)的烯酮与通式(ⅩⅪ)的有机铜化物试剂或者通式(ⅩⅫ)的有机锌试剂反应,可以在催化剂量的乙酰丙酮镍存在下进行反应,
其中R16和Q的定义同上段所规定,
其中R1,R2,X,Y和n的定义同上,
其中R1,R2,X,Y和n的定义同上。
按照文献中叙述的方法可以制备通式(ⅩⅩ)的烯酮。
通式(ⅩⅪ)的有机铜试剂和通式(ⅩⅫ)的有机锌试剂也可按文献中提出的方法制备。
还有一种制备通式(ⅩⅡ)(Z=Z0)的酮的方法,即按照文献中叙述的方法,用通式(ⅩⅩⅣ)的格利雅试剂处理通式(ⅩⅩⅢ)的2-氯酮:
其中Q的定义同上。
其中R1,R2,X,Y和n的定义同上。
制备通式(Ⅵ)的酯的方法是:采用Krapcho(J.Org.Chem.1978,43,138-147)的条件,在湿的二甲基亚砜中,用标准试剂(如氯化锂)使通式(ⅩⅩⅤ)的二酯发生脱羧反应:
(ⅩⅩⅤ)
其中R,R1,R2,Q,X,Y,Z和n的定义同上。
制备通式(ⅩⅩⅤ)的二酯的方法是:在通常溶剂如乙醚,四氢呋喃或二噁烷中,使通式(ⅩⅩⅥ)的化合物与常用的碱如氢化钠或叔丁醇钾反应,
(ⅩⅩⅥ)
其中R1,R2,Q,W,X,Y,Z和n的定义同上。
通式(ⅩⅩⅥ)的化合物可按文献中提出的标准方法制得。
此外,制备通式(Ⅵ)(其中Z=Z0)的酯,也可以用通式(ⅩⅪ)的有机铜化物试剂处理通式(ⅩⅩⅦ)的不饱和酯:
(ⅩⅩⅦ)
其中R和Q的定义同上。
通式(ⅩⅩⅦ)的不饱和酯可以用文献中提出的标准方法制备。
通过已知的方法,可以由通式(Ⅰ)的化合物制得其盐类。
该化合物及其盐都是有效的杀真菌剂,可用于抑制一种或多种下述病原体:
小麦叶锈病,条形柄锈菌和其它锈病;大麦的大麦柄锈菌,条形柄锈菌和其它锈病,其它寄主上如咖啡、苹果、梨、花生、蔬菜和观赏植物的锈病。大麦和小麦白粉病和各种寄主上的其它白粉病,例如南瓜类(如黄瓜)的单丝壳,苹果白粉病和葡萄钩丝壳。长蠕孢类,如谷物的大麦网斑病蠕孢菌,核黑粉菌类和壳针孢类,如小麦颖枯壳针孢。落花生尾孢和例如甜菜、香蕉和大豆上的其它尾孢类,苹果黑星病菌。
有些化合物也表明具有广谱的体外杀真菌活性。它们对水果上的各种收获后病原体具有活性(例如桔子上的绿青霉和柑桔青霉病菌,香蕉盘长孢和葡萄上的灰绿葡萄孢菌)。还有些化合物作为拌种剂对镰孢类、壳针孢类、腥黑穗病(即腥黑粉病、小麦的一种种子寄生病)、黑穗病,和谷物上的长蠕孢类,以及棉花上的马铃薯丝核菌。
该化合物可以在植物组织内向顶部移动。而且,它还有足够的挥发性,可在气相中对植物上的真菌显示出活性。
这些化合物也可用作工业(相对农业来讲)杀真菌剂,例如用以防止真菌侵害木材、皮革、皮革制品、尤其是涂层。
该化合物可直接用于杀真菌目的,但是加工成组合物使用更为方便。于是本发明提供一种杀真菌组合物,它含有前面限定的一种通式(Ⅰ)的化合物或其盐,还可以含有一种载体或稀释剂。
本发明也提供了一种杀真菌的方法,包括将前面限定的一种化合物或其盐施用于植物,植物种子,或者植物或种子所在区域。
有很多种方法施用该化合物或其盐,例如可以加工成制剂或不经加工制剂而直接施用于作物叶子上,或者也可以施用于灌木和树上,种子上或施用于作物、灌木、或树正在生长或将要栽种的介质中,该化合物可以通过喷雾、喷粉或作为霜剂或糊剂施用,或者作为蒸汽使用;也可作为缓释颗粒剂施用。可以施用于作物、灌木或树的任何部位,例如施于叶、茎、枝或根部,或施于根周围的土壤里,或在播种前施于种子;或者一般地施于土壤,施于稻田水或溶液培养体系。本发明化合物也可以注射到作物或树中,也可用电动喷雾技术喷到植被上。
此处所用“植物”一词包括籽苗、灌木和树。而且本发明的杀真菌方法包括防止性的、保护性的,预防性的和根除性的处理方法。
该化合物最好以组合物形式用于农业和园艺方面。所用的组合物的类型总是依照具体的使用目的来确定。
组合物可以是粉剂或颗粒剂,其中含有活性成分和固体稀释剂或载体,例如填料有高岭土,膨润土,白色硅藻土,白云石,碳酸钙,滑石,粉状氧化镁,漂白土,石膏,Hewitt土,硅藻土和瓷土。这些颗粒剂可以制成无须进一步处理即可适合在土壤中使用的颗粒剂。可以通过使填充剂小球中浸入活性成分的方法,或者将活性成分和粉状填充剂的混合物制成小球的方法制成颗粒剂。拌种用的组合物,例如可包括一种增强组合物对种子的附着作用的试剂(如一种矿物油);或者用一种有机溶剂(如N-甲基吡咯烷酮或二甲基甲酰胺)将活性成分加工成适于拌种用的制剂。
该组合物也可以是可分散粉剂、颗粒剂或粒剂形式,其中包括一种润湿剂,以使得粉末或颗粒易于在液体中分散,其中也可以含有填料和悬浮剂。
要制备水分散剂或乳剂,可将活性成分溶于有机溶剂,溶剂中可以含有润湿剂、分散剂或乳化剂,然后将此混合物加入水中,水中也可预先含有润湿剂、分散剂或乳化剂。适合的有机溶剂有二氯乙烷,异丙醇,丙二醇,双丙酮醇,甲苯,煤油,甲基萘,二甲苯类,三氯乙烯,糠醇,四氢糠醇,和乙二醇醚(如2-乙氧基乙醇和2-丁氧基乙醇)。
用作喷雾剂的组合物也可制成气雾剂形式,即将制剂保持在容器中,其中有推进剂如三氯氟甲烷或二氯二氟甲烷存在并具有压力。
该化合物也可以干燥状态与焰熏混合物混合,形成的组合物适用于在密闭空间产生含此化合物的烟雾。
另外,该化合物也可以微胶囊形式使用。它们也可加工成可生物降解的聚合物制剂,以便有控制地、缓慢地释放活性成分。
通过加入适当的添加剂,例如为改进对处理表面的分布性能、附着性能和抗雨淋性能而用的添加剂,所得各种组合物可更好地适用于不同的用途。
该化合物可以与肥料(如含氮、钾或磷的肥料)的混合物形式使用。最好使组合物只含有与该化合物结合(例如涂渍)的肥料颗粒。这种颗粒含有多达25%重量的化合物较合适。因此本发明也提供了一种含有通式(Ⅰ)化合物或其盐的肥料组合物。
该组合物也可制成液体制剂形式用于浸洗或喷雾,一般是水分散剂或乳剂,其中含有活性成分,并有一种或多种表面活性剂如润湿剂、分散剂、乳化剂或悬浮剂存在;或者是适于电动喷雾技术使用的喷雾剂。前面提到的表面活性剂可以是阳离子、阴离子或非离子试剂。适宜的阳离子剂有季铵化合物,例如十六烷基三甲基溴化铵。
合适的阴离子剂有皂类,脂肪基硫酸单酯盐(例如月桂基硫酸钠),磺化芳基化合物的盐(如十二烷基苯磺酸钠,钠,钙或铵的木素磺酸盐,丁基萘磺酸盐,二异丙基和三异丙基萘磺酸钠的混合物)。
合适的非离子剂有环氧乙烷与脂肪醇如油醇或十六醇、或与烷基酚如辛基或壬基酚和辛基甲酚的缩合产物。其它的非离子剂有得自长链脂脂酸和己糖醇酐的部分酯,上述部分酯与环氧乙烷的缩合产物,和卵磷脂。合适的悬浮剂有亲水性胶体(如聚乙烯吡咯烷酮和羧甲基维维素钠),和植物胶(如金合欢胶和黄蓍胶)。
用作水分散剂或乳剂的组合物一般是以其浓集物形式提供的,其中含有很高比例的活性成分,该浓集物在使用前要用水稀释。这些浓集物一般应能耐长期贮存,而且长期贮存后仍能用水稀释而形成含水制剂,该含水制剂应能在足够长的时间内保持均匀以便用通常的和电动的喷雾设备施用。该浓集物通常可以含有高达95%、较好是10-85%、例如25-60%(重量)的活性成分。这些浓集物最好含有有机酸(如烷芳基或芳基磺酸,如二甲苯磺酸或十二烷基苯磺酸),这是因为这些酸的存在可以增加活性成分在浓集物中常常使用的极性溶剂中的溶解度。浓集物中最好还含有高比例的表面活性剂,以便在水中可以得到充分稳定的乳剂。根据不同的使用目的,稀释后形成的含水制剂中可以含有不同量的活性成分,但是含有0.0005%或0.01%到10%(重量)活性成分的含水制剂是可以采用的。
本发明的组合物还可以含有其它具有生物活性的化合物,如具有相似的或互补的杀真菌作用的化合物,或者具有植物生长调节、除草或杀虫活性的化合物。
其它的杀真菌化合物可以是能杀灭谷物(如小麦)的下列穗病的化合物:如壳针孢属,赤霉属和长蠕孢属,种子和土壤寄生的病菌,和葡萄上的霜霉和白粉菌,苹果上的白粉菌或斑点病等。这些杀真菌剂混合物比单独的通式(Ⅰ)的化合物具有更广谱的活性;况且另一种杀真菌剂可以对通式(Ⅰ)化合物的杀真菌活性具有协同作用。其它杀真菌化合物的例子有多菌灵,苯菌灵,甲基托布津,涕必灵,麦穗宁,etridazole,抑菌灵,Cymoxanil,oxadixyl,ofurace,metalaxyl,furalaxyl,benalaxyl,fosetyl-aluminium,双氯苯嘧啶,iprodione,procymidione,vinclozolin,penconazole,myclobutanil,R0151297,定菌磷,乙菌定,灭菌磷,环吗啉,嗪胺灵,nuarirnol,triazbutyl,双胍盐,1,1′-亚氨基二(八亚甲基)二胍三乙酸盐,propiconazole,prochloraz,flutriafol,hexaconazole即化学品1-(1,2,4-三唑-1-基)-2-(2,4-二氯苯基)己-2-醇,(2RS,3RS)-2-(4-氯苯基)-3-环丙基-1-(1H,1,2,4-三唑-1-基)J-2-醇,(RS)-1-(4-氯苯基)-4,4,4-二甲基-3-(1H-1,2,4-三唑-1-基甲基)-戊-3-醇,DPX H6573(1-((双-4-氟苯基)甲基甲硅烷基)甲基)1H-1,2,4-三唑,三唑二甲酮,triadimenol,diclobutrazol,fenpropimorph,fenpropidin,Chlorozolinate,diniconazol,imazalil,一甲呋萎灵,萎锈灵,氧化萎锈灵,methfuroxam,环烷吗啉,BAS454,灭瘟素,春日霉素,克瘟散,异稻瘟净,放线菌酮,四氯苯酞,噻菌烯,稻瘟灵,三唑苯噻,pyroquilon,4-氯-N-(氰基(乙氧基)甲基苯甲酰胺,chlorbenzthiazone,甲胂酸铁铵,多氧霉素,有效霉素,mepronil,flutolanil,pencycuron,diclomezine,叶枯净,二甲基二硫代氨基甲酸镍,techlof thalam,bitertanol,磺酸丁嘧啶,etacenazole,链霉素,Cypofuram,biloxazol,甲基克杀螨,甲嘧醇,1-(2-氰基-2-甲氧亚氨基乙酰基)-3-乙基脲,fenapanil,tolclofosmethyl,pyroxyfur,代森联,代森锰,代森锰锌,敌菌丹,百菌清,敌菌灵,福美双,克菌丹,灭菌丹,代森锌,甲基代森锌,硫磺粉,消螨普,乐杀螨,nitrothal-isopropyl,十二烷胍,二噻农,氢氧三苯基锡,乙酸三苯基锡,四氯硝基苯,五氯硝基苯,氯硝胺,含铜化合物如氧氯化铜,硫酸铜和波尔多液,和有机汞化合物。
通式(Ⅰ)的化合物可以与土壤、泥炭或其它生根的介质混合,以保护植物免受种子寄生、土壤寄生或叶部的真菌的危害。
可以混合于本发明组合物的合适的杀虫剂包括灭定威,乐果,异吸硫磷Ⅱ,安果,西维因,异丙威,二甲威,丁苯威,呋喃丹,Carbosulfan,二嗪农,倍硫磷,杀螟松,稻丰散,氯蜱硫磷,异噁唑硫磷,丙虫磷,久效磷,buprofezin,ethroproxyfen和cycloprothrin。
用于本发明组合物中的植物生长调节化合物是抑制害草或籽芽形成的化合物,或选择性地抑制有害植物(如杂草)生长的化合物。
用于本发明组合物的合适的植物生长调节化合物有:赤霉酸(如GA3,GA4或GA7),植物生长激素类(如吲哚乙酸,吲哚丁酸,萘氧乙酸或萘乙酸),细胞分裂素(如激动素,二苯基脲,苯并咪唑,苄基腺嘌呤),苯氧乙酸类(如2,4-滴或2甲4氯),取代的苯甲酸类(如三碘苯甲酸),整形素(如氯芴素),马来酰肼,草甘膦,催熟膦,长链脂肪酸和醇,dikegulac,paclobutrazol,flurprimidol,氟磺安,mefluidide,取代的季铵或鏻化合物(如Chloromequat Chlorphonium或mepiquatchloride),乙烯利,草威安,甲基-3,6-二氯茴香酸盐,二甲基琥珀酰肼,黄草灵,abscisic酸,isopyrimil,1-(4-氯苯基)-4,6-二甲基-2-氧代-1,2-二氢吡啶-3-羧酸,羟基苄腈类(如溴草腈),离子草吡唑,新燕灵,敌草定,fenpentezol,inabenfide,triapenthenol和四氯硝基苯。
用下面的实例说明本发明,所给温度为摄氏度。
例1
这个例子是阐明4-〔3-(对-叔丁基苯基)-顺式-环丁基甲基〕-2,6-顺式-二甲基吗啉的制备方法(见表1的化合物No.3.1)。将对-叔丁基苯甲基溴(20.44g,0.09mol)和氰化钾(11.72g,0.18ml)置于18-冠醚-6(50ml)饱和溶液中在80℃下回流5小时。冷却到室温后,将溶液倒入水中,用二氯甲烷萃取。有机相用无水硫酸钠干燥。去溶剂后剩下黄色液体,再经柱层析纯化〔固定相是SiO2,用石油醚-乙酸乙酯,(9∶1)淋洗〕得到对-叔丁基苄基氰(15.4g,99%)。
将对-叔丁基苄基氰(28.6g,0.166mol)和浓硫酸(60.7g)的无水乙醇(60.7g)溶液在100℃下回流7小时。将混合物倒入水中,用乙醚萃取,有机相加无水硫酸钠干燥。去溶剂后即得到对-叔丁基苯基醋酸乙酯,(32.3g,89%)的无色液体。
将对-叔丁基苯基醋酸乙酯(32.29g,0.147mol),碳酸二乙酯(7.1g,0.309mol)和乙醇钠(21g,0.309mol)的甲苯溶液(140ml)置于Dean-Stark装置里,回流6小时。真空蒸去甲苯后的油状物倒入水中,用乙醚萃取,有机相用无水硫酸钠干燥。去溶剂后的褐色油状物经柱层析纯化〔填料是SiO2,用4∶1的石油醚-乙酸乙酯淋洗〕,得到对-叔丁基苯基丙二酸二乙酯(29.0g,68%)的无色液体。
将对-叔丁基苯基丙二酸二乙酯(27.6g,0.095mol)的乙醚溶液(乙醚用金属钠干燥过,300ml)滴加到氢化铝锂(8.3g,0.218mol)的乙醚悬浮液中(乙醚用金属钠干燥过,300ml),控制滴加速度,以维持和缓的回流状态。加完后,在室温下搅拌6小时。小心将溶液转移到水中,用2MHCl酸化,再用乙醚萃取。醚提物用水洗涤,并用无水硫酸钠干燥,去溶剂后即得到2-(对-叔丁基苯基)-1,3-丙二醇(18.8g,95%)的黄色固体,供下步使用、不需纯化。
在低于10℃的温度下,将对-甲苯磺酰氯(38.5g,0.202mol)加到2-(对-叔丁基苯基)-1,3-丙二醇(18.84g,0.09mol)的无水吡啶(100ml)溶液中。12小时后,在20℃下,混合物用冷盐酸处理,滤出固体。
将上述固体在乙醇中重结晶,则制得2-(对-叔丁基苯基)-1,3-丙二醇的二-对-甲苯磺酸酯(33.8g,73%)白色固体结晶,其熔点为135-136℃。
将氢化钠(3.1g,0.065mol;50%的矿物油悬浮液)的二氧六环悬浮液(无水二氧六环,40ml),在一个多小时的时间内,一滴一滴地加到2-(对-叔丁基苯基)-1,3-丙二醇-二-对-甲苯磺酸酯(33.8g,0.0654mol)和丙二酸二乙酯(11.41g,0.0712mol)的无水二氧六环溶液中(150ml)。在氮气气氛中让热到接近开始回流。控制滴加的速度,使反应产生的热量,引起自发回流。在搅拌情况下回流1小时后,再滴加氢化钠(31.0g,0.065mol,50%的矿物油悬浮液)的无水二氧六环悬浮液(40ml),小心操作,用3小时加完。回流10小时,减压蒸去二氧六环。残渣用水处理,乙醚萃取,醚提物用无水硫酸钠干燥。去溶剂后的褐色树脂状物经柱层析纯化(填料为SiO2,用4∶1的石油醚-乙酸乙酯淋洗)得3-(对-叔丁基苯基)环丁-1,1-二羧酸二乙酯的无色油状物(12.9g,60%)。
将3-(对-叔丁基苯基)环丁-1,1-二羧酸二乙酯(8.25g,0.025mol),氯化锂(2.3g,0.054mol),水(30ml,1.67mol)和二甲亚砜(50ml)在140-150℃加热12小时。将混合物冷却,倒入水中,用乙酸乙酯萃取,水洗有机相,并用无水硫酸钠干燥。去溶剂,并经柱层析纯化(填料为SiO2,用4∶1的石油醚-乙酸乙酯淋洗)得到3-(对-叔丁基苯基)环丁-1-羧酸乙酯(4.55g,70%)。
将3-(对-叔丁苯基)环丁-1-羧酸乙酯(4.5g,0.017mol)溶于甲醇中(40ml),并在室温下滴加氢氧化钾(1.9g,0.034mol)的水溶液(40ml)。将溶液回流3小时,冷却到室温,并仔细用2M盐酸中和。乙酸乙酯萃取后,有机相用水洗涤,并用无水硫酸钠干燥。去溶剂后得到3-(对-叔丁基苯基)环丁-1-羧酸(3.84g,97%)的黄色固体。
将3-(对-叔丁基苯基)环丁-1-羧酸(3.84g,0.0166mol)和草酰氯(3g,0.024mol)混于己烷中(30ml),在室温下搅拌1小时,并在60℃温度下加热3小时。真空蒸去己烷和过剩的草酰氯得到3-(对-叔丁基苯基)环丁-1-碳酰氯的淡黄色液体(4.14g,100%),供下步使用,不需纯化。
在10℃下,将2,6-二甲基吗啉(4.6g,0.04mol)滴加到3-(对-叔丁基苯基)环丁-1-碳酰氯(3.0g,0.012mol)的乙醚溶液中(经金属钠干燥过的乙醚,20ml),加完后,在20℃下搅拌3小时。将反应的混合物倒入水中,用乙醚萃取(两次,每次50ml)。醚提物用水洗,并用无水硫酸钠干燥。去溶剂后得到3-(对-叔丁基苯基)环丁-1-碳酰(2,6-二甲基吗啉)(3.88g,98%)。
将3-(对-叔丁基苯基)环丁-1-碳酰(2,6-二甲基吗啉)(3.63g,0.011mol)的乙醚溶液(金属钠干燥过的乙醚50ml)滴加到氢化铝锂(0.8g,0.021mol)的乙醚悬浮液中(金属钠干燥过的乙醚25ml),在室温下搅拌3小时。将反应的混合物小心地倒入水中,用乙醚萃取。醚提物用水洗后用无水硫酸钠干燥,去溶剂后得到无色油状物。
上述油状物经柱层析纯化(填料为SiO2,用9∶1石油醚-乙酸乙酯啉洗)即得到标题化合物(0.9g,26%)。它的三个异构体(在表1中的化合物号为1.1,2.1和4.1)亦被分离出来。
例2
这个例子是阐明4-〔反式-3-(4-三甲硅苯基)环丁甲基〕-顺式-2,6-二甲基吗啉(表1中的化合物编号NO.15.1)的制备。在氮气气氛里,在搅拌的情况下,将正丁基锂(1.6M的己烷溶液87.5ml,140mmol)滴加到4-溴苯乙烯(25.0g,137mmol)的干燥四氢呋喃溶液中(187ml),控制滴加的速度,保持温度低于-60℃。一个半小时以后,温度可以升高到-55℃,并滴加三甲基氯硅烷(17.5ml,138mmol)。30分钟后,混合物的温度可以升到室温,并加入乙酸乙酯(1ml)。然后将混合物倒入水中。分出有机相,用水洗三次,再用盐水洗一次,加无水硫酸镁干燥后,真空蒸去溶剂,得到4-三甲硅烷基苯乙烯(24.1g,100%),不需纯化。
用30分钟时间,将三氯乙酰氯(25ml,224mmol)的干燥乙醚(100ml)溶液加到锌粉(19.5g,300mmol)和4-三甲硅烷基苯乙烯(25.8g,147mmol)在300ml干燥乙醚的混合物中,反应在声波槽内进行,一小时左右,薄层层析表明原料已反应完。混合物用硅藻土担体过滤。滤液用水洗,饱和碳酸氢钠洗,再用水洗,加无水硫酸镁干燥,最后真空蒸去溶剂。层析后(填料SiO2,用95∶5的己烷-乙酸乙酯淋洗)得到2,2-二氯-3-(4-三甲硅苯基)环丁酮(6.1g,15%),熔点65-69℃。
在氮气气氛下,将2,2-二氯-3-(4-三甲硅苯基)环丁酮(6.1g,21mmol)和偶氮双异丁腈(0.1g)混于环己烷中(15ml)加入到正在回流状态的氢化三丁基锡(12.5ml,47mmol)的环己烷(15ml)溶液中。三小时后,将混合物冷却,真空蒸发,再经层析后〔填料SiO2,淋洗剂为己烷-乙酸乙酯(100∶0)到(80∶20)〕得到3-(4-三甲硅苯基)环丁酮(3.30g,71%),熔点48℃。
在氩气气氛下,将二甲亚砜(10ml)加到己烷洗过的氢化钠中(50%的在油里的悬浮液,0.73g,16mmol)。将混合物加热到70℃,维持1小时,冷却到0℃,再加四氢呋喃(11ml)。分批加入甲基三苯基溴化鏻(5.7g,16mmol)。30分钟后,缓慢地加入3-(4-三甲硅苯基)环丁酮(3.3g,15mmol)。24小时后,将混合物倒入水中,用己烷萃取。萃取物用水洗,无水硫酸镁干燥,真空蒸干。再经层析后(填料SiO2,己烷淋洗)得到3-(4-三甲硅苯基)-1-亚甲基环丁烷(1.33g,41%)。
在0℃,氮气气氛下,将甲硼烷(1.0M的四氢呋喃溶液2.15ml,2.15mmol),加到正在搅拌的3-(4-三甲硅苯基)-1-亚甲基环丁烷(1.33g,6.2mmol)的四氢呋喃(20ml)溶液中。30分钟后,混合物加热到室温,加完3M氢氧化钠溶液后(0.75ml,2.25mmol),再滴加过氧化氢溶液(30%(重量/体积)0.9ml,7.9mmol)。将混合物加热到60℃,2小时后冷却到室温,再加入乙醚。混合物先后用水和盐水洗涤,无水硫酸镁干燥,真空蒸干。经层析后(填料SiO2,淋洗液己烷-乙酸乙酯(100∶0)到(50∶50)〕得到3-(4-三甲硅苯基)环丁基甲醇(0.89g,62%)。
在-78℃下,将草酰氯(0.83ml,9.5mmol)滴加到二甲亚砜(0.83ml,11mmol)的干燥二氯甲烷(24ml)溶液中。15分钟后,将3-(4-三甲硅苯基)环丁基甲醇(0.89g,3.8mmol)的干燥二氯甲烷(15ml)溶液加入混合物中。1小时后,加入三乙胺(4.2ml,30mmol),并加热到室温。加入己烷(100ml)和水(100ml),分出有机相,水洗6次,无水硫酸镁干燥,真空蒸发后得3-(4-三甲硅苯基)环丁基甲醛(Carboxaldeyde)(0.82g,93%)。
在氮气气氛下将2.5M氯化氢甲醇溶液(3.5ml,8.7mmol)加到正在搅拌的3-(4-三甲硅苯基)环丁基甲醛(0.82g,3.5mmol),顺式-2,6-二甲基-吗啉(2.43g,21mmol),氰基硼氢四丁基铵(1.50g,5.3mmol)和4 分子筛(1g)在无水二氯甲烷(8ml)中的混合物里。16小时后,将混合物过滤(用硅藻土),用2M氢氧化钠溶液洗3次,水洗6次,无水硫酸镁干燥,真空蒸干。层析后〔填料SiO2,淋洗液是己烷-乙酸乙酯(80∶20)〕得到4〔反式-3-(4-三甲硅苯基)-环丁甲基〕-顺式-2,6-二甲基吗啉(0.264g,23%)。顺式异构体(在表1中化合物编号为NO.14.1)亦被分离出来(0.368g,32%)。
例3
这个例子是阐述4-〔3-(对-异丙基苯基)环戊甲基〕-2,6-顺式-二甲基吗啉的制备方法(在表Ⅱ中,化合物编号是NO.1,2)。将丁二酸酐(20g,0.2mol)放到异丙苯中(60g,0.5mol)并搅拌。将氯化铝粉末(53.3g,0.4mol)用在15分钟分批加入。加完后,将此悬浮液加热到80℃,保持10小时,然后冷却到室温。将得到的深红色油状物小心地倒入冰水中,并用乙酸乙酯萃取三次(每次200ml)。有机相用饱和的碳酸氢钠洗三次(每次用150ml)。水相用浓盐酸酸化后再用乙酸乙酯萃取,无水硫酸钠干燥,真空去溶剂后得到白色固体。白色固体经冰冷的石油醚洗涤,得到4-(对-异丙苯基)-4-氧代-丁酸的白色晶体(30g,68%),熔点140-141℃。
在室温下,将硝酸铊(Tl,Ⅲ价)(44.4g,0.1mol)与4-(对-异丙苯基)-4-氧代-丁酸(22.0g,0.1mol)一起放入原甲酸三甲酯中(500ml)搅拌,并滴加高氯酸(40g,0.4mol)。由于反应放热,温度升到40℃,产生硝酸铵(Ⅰ价铊)白色沉淀。在室温下搅拌4小时,滤出铊盐,溶液用乙醚萃取。醚提物用水洗后,加无水硫酸钠干燥。去溶剂后的黄色油状物经柱层析(填料SiO2,用3∶7乙酸乙酯-石油醚淋洗)得对-异丙苯基丁二酸二甲酯淡黄色油状物(18.0g,68%)。
将氢化铝锂(4.6g,0.12mol)悬浮于经金属钠干燥过的乙醚中(150ml),再滴加对-异丙苯基丁二酸二甲酯(13.2g,0.05mol)的乙醚溶液(100ml,乙醚经金属钠干燥过),控制滴加速度,维持体系处于和缓的回流状态。溶液在室温下搅拌4小时,小心地倒入水中,用浓盐酸酸化,并用乙酸乙酯萃取三次(每次150ml)。有机相经水洗,无水硫酸钠干燥后,真空去溶剂得到2-(对-异丙苯基)-1,4-丁二醇黄色油状物(10.0g,96%)。
在5℃下,将2-(对-异丙苯基)-1,4-丁二醇(4.16g,0.02mol)放入干燥吡啶中(10ml)搅拌,再于室温下滴加甲磺酰氯(4.6g,0.04mol)。温度升到30℃,加完后再在室温下搅拌3小时。将反应混合物倒入水中,用乙醚萃取2次(每次100ml)。有机相先后用2M盐酸洗2次(每次100ml)和水洗2次(每次100ml),再用无水硫酸钠干燥。去溶剂后得到的白色晶体与石油醚一起研磨,过滤,并干燥则得到2-(对异丙苯基)-1,4-丁二醇-的二甲磺酸酯(7.0g,96%),熔点80-81℃。
在氮气气氛下,将氢化钠(0.72g,0.015mol;50%矿物油悬浮液)的干燥二氧六环(5ml)悬浮液,在半小时的时间内滴加到2-(对-异丙苯基)-1,4-二丁醇-二甲磺酸酯(5.22g,0.015mol)和丙二酸二乙酯(2.72g,0.017mol)的干燥二氧六环(30ml)溶液中去,加热到接近回流状态,控制滴加速度,以使其自发的回流。在搅拌下回流1小时后,加入另一分氢化钠(0.72g,0.015mol;50%矿物油悬浮液)的干燥二氧六环(5ml)溶液,在一小时内小心地加完。混合物回流15小时,减压蒸去二氧六环。残渣用水处理后,用乙醚萃取,加无水硫酸钠干燥。去溶剂后的橙色油状物经柱层析纯化(填料SiO2,用9∶1的石油醚-乙酸乙酯淋洗)得到3-(对-异丙苯基)环戊-1,1-二羧酸二乙酯(3.0g,64%)的无色液体。
将3-(对-异-丙苯基)环戊-1,1-二羧酸二乙酯(2.11g,0.00653mol)、氯化锂(0.54g,0.013mol)、水(0.114g,0.00635mol)和二甲亚砜(11ml)的混合物加热回流4小时。然后将其冷却,倒入水中,用乙醚萃取,水洗后,加无水硫酸钠干燥。去溶剂后得到3-(对-异丙苯基)环戊-1-羧酸乙酯(0.92g,56%)。
将3-(对-异丙苯基)环戊-1-羧酸乙酯(0.81g,0.003mol)溶于甲醇中(8ml),在室温下滴加氢氧化钾(0.35g,0.006mol)的水溶液(8ml)。将此溶液回流3小时后,冷却到室温,小心地用2M盐酸中和。乙酸乙酯萃取后的有机相用水洗涤,加无水硫酸钠干燥。去溶剂后得到3-(对-异丙苯基)环戊酸的浅褐色油状物(0.63g,87%)。
将3-(对-异-丙苯基)环戊酸(0.52g,0.002mol)和草酰氯(0.4g,0.003mol)混合于己烷中(4ml),在室温下搅拌1小时,再在60℃下加热3小时。真空蒸去己烷和过剩的草酰氯得到3-(对-异丙苯基)环戊-1-酰氯的黄色液体(0.55g,100%),供下步使用不需纯化。
在10℃下,将顺-2,6-二甲基吗啉(0.97g,0.0085mol)滴加到3-(对-异丙苯基)环戊-1-酰氯(0.53g,0.0021mol)的钠干燥过的乙醚溶液中(4ml),加完后,在20℃下搅拌3小时。反应混合物倒入水中,用乙醚萃取2次(每次50ml)。有机相经水洗,无水硫酸钠干燥,去溶剂后得到3-(对-异丙苯基)环戊-1-酰-(2,6-顺-二甲基吗啉(0.61g,88%)。
将3-(对-异丙苯基)环戊-1-酰-(2,6-顺-二甲基吗啉)(0.51g,0.0016mol)的钠干燥过的乙醚(3ml)溶液滴加到氢化铝锂(0.088g,0.0023mol)的钠干燥过的乙醚(3ml)悬浮液中,在室温下搅拌3小时。小心将反应混合物倒入水中,用乙醚萃取。有机相用水洗,无水硫酸钠干燥后,去溶剂得无色油状物。此油状物经柱层析纯化(填料SiO2,用7∶3石油醚-乙酸乙酯淋洗)即得到所需要的化合物(0.41g,84%)该化合物为无色油状物。
例4
这个例子是阐明4-〔3-(对-S-丁苯基)环戊甲基-顺-2,6-二甲基吗啉的制备方法(在表Ⅱ中化合物编号是NO.8.2)。将丁二酸酐(20g,200mmol)放入S-丁苯中(87g,500mmol),进行搅拌。在室温下,5分钟时间里分批加入粉末状氯化铝(53.3g,400mmol)。然后将混合物加热到80℃。10小时后冷却到室温。再将混合物小心地倒入冰水中,用乙酸乙酯萃取三次。合并有机相,用饱和碳酸氢钠洗三次。水相用浓盐酸酸化,再用乙酸乙酯萃取三次。合并两次萃取的有机相,先后用水和盐水洗涤,经无水硫酸钠干燥,真空蒸发去溶剂后得到浅褐色固体。用冷的石油醚(15ml)反复洗涤即得到4-(对-S-丁苯基)-4-氧代-丁酸的白色晶体(13.0g,28%)。
在室温下,将高氯酸(17.17g,171mmol)滴加到4-(对-S-丁苯基)-4-氧代-丁酸(10.0g,42.7mmol)、原甲酸三甲酯(180ml)、和硝酸铊(18.99g,42.7mmol,铊是Ⅲ价)的正在搅拌的混合物中。4小时后,将混合物过滤,滤液用乙醚萃取。有机相用水洗涤,加无水硫酸钠干燥,真空蒸干。层析后〔填料SiO2,淋洗液是石油醚-乙酸乙酯(90∶10)到(70∶30)〕得到对-S-丁苯基丁二酸二乙酯(8.82g,74%)。
将对-S-丁苯基丁二酸二甲酯(12.1g,43.5mmol)的干燥乙醚溶液(75ml)加到正在搅拌的氢化铝锂(4.01g,105.6mmol)的干燥乙醚悬浮液中(75ml),控制加的速度,维持体系处于和缓的回流状态。4小时后,在室温下,将混合物小心地倒入水中,用浓盐酸酸化,再用乙醚萃取三次。合并的有机相先后用2M盐酸洗一次,水洗三次,加无水硫酸钠干燥,真空蒸发后得到2-(对-S-丁苯基)-1,4-丁二醇(0.51g,98%)。
在5℃时将甲磺酰氯(9.55g,83.4mmol)缓慢地加到正在搅拌的2-(对-S-丁苯基)-1,4-丁二醇(9.25g,41.7mmol)的干燥三乙胺溶液中去。在室温下搅拌10小时以后,将混合物倒入水中,用乙醚萃取三次。合并有机相,先后用水洗,2M盐酸洗两次,再用水洗一次,用无水硫酸钠干燥后,减压蒸发得褐色油状物。将此油状物与石油醚-乙醚(90∶10)共研,得到2-(对-S-丁苯基)-1,4-丁二醇-二甲磺酸酯(8.46g,54%),供下步使用,不需纯化。
将氢化钠(1.06g,50%油分散液22.1mmol)分批加到正在搅拌的2-(对-S-丁苯基)-1,4-丁二醇-二甲磺酸酯(8.35g,22.1mmol)和丙二酸二乙酯(4.07g,25.4mmol)的干燥二氧六环(45ml)溶液中,控制加料速度以维持和缓的回流状态。在回流状态下搅拌一小时以后,小心地加入氢化钠(1.06g,50%油分散液22.1mmol)。再在回流状态下搅拌8个小时后,将混合物冷却,并减压蒸发。将水加入残渣中,用乙醚萃取两次。合并有机相,先后用水和盐水洗涤,无水硫酸钠干燥,并真空蒸发。层析后(填料SiO2,用90∶10的石油醚-乙酸乙酯淋洗)得到3-(对-S-丁苯基)环戊-1,1-二羧酸二乙酯(2.51g,33%)。
将3-(对-S-丁苯基)环戊-1,4-二羧酸二乙酯(2.32g,13.4mmol)、氯化锂(0.57g,13.4mmol)、水(0.121g,6.7mmol)和二甲亚砜(11ml)混合物回流3小时。将混合物倒入水中,水相用氯化钠饱和。用己烷萃取混合物4次,合并的有机相用盐水洗,无水硫酸钠干燥,并真空蒸发。层析后〔固定相SiO2,淋洗液石油醚-乙酸乙酯(90∶10)〕得到3-(对-S-丁苯基)环戊-1-羧酸乙酯(1.28g,77%)。
将氢氧化钾(0.47g,8.4mmol)的水溶液(11ml)加入3-(对-S-丁苯基)环戊-1-羧酸乙酯(1.15g,4.2mmol)的甲醇(11ml)溶液中。经搅拌1小时后,回流5小时,冷却,加2M盐酸酸化,用乙酸乙酯萃取。有机相用盐水洗涤,无水硫酸镁干燥,真空蒸发得到3-(对-S-丁苯基)环戊-1-羧酸(1.08g,100%)。
在一分钟时间内将草酰氯(1.20g,9.45mmol)滴加到正在搅拌的3-(对-S-丁苯基)环戊-1-羧酸(0.93g,3.78mmol)的石油醚悬浮液中(7ml)。在室温下保持1小时后,回流8小时,冷却,用硅藻土过滤。将滤液真空蒸发即得到3-(对-S-丁苯基)环戊-1-酰氯(1.12g,100%),供下步使用,不需纯化。
在5℃下,将顺-2,6-二甲基吗啉(1.84g,16mmol)滴加到正在搅拌的3-(对-S-丁苯基)环戊-1-酰氯(1.06g,4mmol)的干燥乙醚(8ml)溶液中。室温下保持4小时,将混合物倒入水中,用乙醚萃取。合并的有机相先后用饱和的碳酸氢钠溶液、水和盐水洗涤,无水硫酸钠干燥,并真空蒸发得到3-(对-S-丁苯基)环戊-1-酰-(2,6-顺-二甲基吗啉)(1.26g,92%)供下步使用,不要纯化。
将3-(对-S-丁苯基)环戊-1-酰-(2,6-顺-二甲基吗啉)(1.05g,3.06mmol)的干燥乙醚(5ml)溶液,滴加到正在搅拌的氢化铝锂(0.193g,5.07mmol)的干燥乙醚(5ml)溶液中,控制加料速度,以维持稳定的泡腾状态。在室温下保持2小时,将混合物小心地加入水中,用乙醚萃取。合并的有机相先后用水和盐水洗涤,用无水硫酸钠干燥,并真空蒸发。层析后〔固定相SiO2,淋洗液石油醚-乙酸乙酯(70∶30)〕得到4-〔3-(对-S-丁苯基)环戊甲基〕-顺-2,6-二甲基吗啉(0.91g,90%)的无色油状物。
例5
这个例子是阐明4-〔3-(4-氯苯基)环戊甲基〕-2,6-顺-二甲吗啉的制备方法(在表Ⅱ中化合物编号为14.2)。在0℃,氮气气氛下,将正丁基锂(1.55M的己烷溶液26ml,40.3mmol)滴加到正在搅拌的4-溴氯苯(7.66g,40mmol)的无水乙醚溶液(60ml)中。在室温下,一小时后将混合物加到无水溴化锌(4.5g,20mmol)的干燥乙醚液(20ml)中,当所有的溴化锌被溶解后,将混合物放到声波槽上反应30分钟。将2-环戊酮(0.82g,10mmol)和乙酰丙酮镍(0.06g,0.2mmol)的乙醚溶液(10ml)加到正在搅拌的混合物中。在室温下保持1小时后,将混合物加到氯化铵饱和水溶液中,用乙醚萃取。合并的有机相用硫酸镁干燥后,真空蒸发。层析后〔固定相SiO2,流动相己烷-乙酸乙酯(80∶20)〕得到3-(4-氯苯基)-环戊酮(1.03g,53%)。
在氮气氛下,将二甲亚砜(5ml)加到己烷洗涤过的氢化钠中(0.461g,55%的油悬浮液,10.6mmol),并在70℃下,搅拌1小时。将混合物冷却到0℃,加四氢呋喃(10ml),再加溴化甲基三苯基鏻(3.786g,10.6mmol)。搅拌1小时后,加入3-(4-氯苯基)-环戊酮(1.03g,5.3mmol)的四氢呋喃溶液(5ml)。在0℃保持3小时,加入己烷,用硅藻土过滤。将滤液真空蒸干,再经层析(固定相SiO2,淋洗液己烷)得到3-(4-氯苯基)-1-亚甲基环戊烷(0.56g,55%)。
在0℃,氮气氛下将甲硼烷(1M的四氢呋喃溶液1.0ml,1mmol)加到正在搅拌的3-(4-氯苯基)-1-亚甲基环戊烷(0.56g,2.9mmol)的四氢呋喃中(10ml)。30分钟后,混合物的温度可以升到室温,滴加3M氢氧化钠(0.34ml,1.02mmol),接着滴加过氧化氢(30%水溶液W/V,0.43ml,3.8mmol)。将混合物加热到60℃,30分钟后冷却到室温,用乙醚萃取。合并有机相,先后用水和盐水洗涤,硫酸镁干燥,再真空蒸干。层析后〔固定相SiO2,淋洗液己烷-乙酸乙酯(50∶50)〕得到3-(4-氯苯基)-1-(羟甲基)-环戊烷(0.342g,53%)。
在氮气氛下,将二甲亚砜(0.35ml,4.9mmol)加入干燥二氯甲烷(10ml)中,冷却到-78℃,再滴加草酰氯(0.35ml,4.0mmol)。15分钟后,再加入3-(4-氯苯基)-1-(羟甲基)-环戊烷(0.342g,1.6mmol)的干燥二氯甲烷溶液(5ml)。再过1小时,加入三乙胺(1.78ml,128mmol),并让混合物温度提高到室温。将己烷和水加到混合物中,并通过硅藻土过滤。有机相经水洗6次,干燥,真空蒸发后得到3-(4-氯苯基)环戊基甲醛(0.326g,98%,供下步使用,不需纯化。
将氯化氢的甲醇溶液(2.6M溶液3.5ml,9.1mmol)加到正在搅拌的3-(4-氯苯基)环戊基甲醛(0.326g,1.56mmol),氰基硼氢化四丁基铵盐(0.884g,3.1mmol),顺-2,6-二甲基吗啉(2.21g,19.2mmol)和4A分子筛(1.5g)在干燥二氯甲烷中的混合物里(20ml)。17个小时后,将反应混合物过滤,滤液用2M的氢氧化钠洗三次。水相用乙醚萃取。合并有机相,用水洗四次,硫酸镁干燥,并真空蒸干。层析后(固定相SiO2,淋洗液己烷-乙酸乙酯(70∶30)〕得到4-〔3-(4-氯苯基)环戊甲基〕-2,6-顺式-二甲基吗啉(0.262g,55%),顺反异构体各占50%。
例6
这个例子是阐明4-〔反-2-(4-叔丁苯基)环丁甲基〕-2,6-顺-二甲基吗啉的制备方法(表Ⅲ中化合物编号是1.3)。将镁(4.86g,200mmol)加到正在搅拌的对-叔丁基肉桂酸甲酯(10.5g,48.1mmol)的干燥甲醇(500ml)溶液中,加热到40℃以引发反应。一旦反应开始,将温度保持在20℃左右,持续2小时则反应完全。加入己烷(100ml)和乙醚(10ml),接着加2M盐酸使沉淀溶解。分出有机相,用水洗6次,加无水硫酸钠干燥后,真空蒸发,并通过硅胶过滤,得到3-(4-叔丁苯基)丙酸甲酯(9.0g,82%)。
在10分多钟的时间内,将氢化二异丁基铝(约30.7ml的约2M甲苯溶液,约46.0mmol)滴加到正在搅拌的-78℃的3-(4-叔丁苯基)丙酸甲酯(9.0g,40.9mmol)的无水甲苯溶液中(100ml)。2.5小时后,加入甲醇(10ml),并让温度上升到室温。加入2M盐酸使沉淀溶解,分出有机相,用水洗5次,无水硫酸钠干燥,真空蒸干。层析后〔固定相SiO2,淋洗液为叔丁基甲基醚-己烷(10∶90)到(40∶60)〕得到3-(4-叔丁基苯基)-1-丙醇(4.1g,52%)。
将三苯基膦(11.23g,85.2mmol)加入3-(4-特丁基苯基)-1-丙醇(4.1g,21.3mmol)的1,2-二氯乙烷溶液中(18ml),并将混合物冷却到-15℃。用10分钟时间,将1,2-二溴四氯乙烷(13.94g,42.6mmol)的1,2-二氯乙烷溶液(24ml)和三乙胺(8.65ml,42.6mmol)同时加入。20分钟以后,让混合物的温度升到室温,真空蒸发,加二氯甲烷溶解,水洗三次后再用盐水洗涤,真空蒸发。残渣加乙醚溶解,通过硅藻土担体过滤,真空蒸发,经层析后〔固定相SiO2,淋洗液叔丁基甲基醚-己烷(1∶99)〕得到1-溴-3-(4-叔丁基苯基)丙烷(4.60g,85%)。
将1-溴-3-(4-叔丁苯基)丙烷(4.51g,17.7mmol),N-溴代丁二酰亚胺(3.15g,17.7mmol)和偶氮双异丁腈(100mg),置于四氯化碳中(40ml),用60W灯泡照射,使之回流2小时。然后将混合物冷却,用硅藻土担体过滤,真空蒸发,并经层析后(固定相SiO2,淋洗液己烷)得到1,3-二溴-1-(4-叔丁基苯基)丙烷(3.0g,51%)。
将1,3-二溴-1-(4-叔丁基苯基)丙烷(3.0g,9.0mmol)和丙二酸二乙酯(1.52g,9.5mmol)溶于无水的二氧六环中(20ml),并加热到90℃。在5分钟时间内,滴加经己烷洗涤过的氢化钠(0.432g,50%的油悬浮液,9.0mmol)的干燥二氧六环溶液(3ml),维持回流状态。回流1小时。再在5分钟时间内,滴加经己烷洗过的氢化钠(0.432g,50%的油悬浮液,9.0mmol)的干燥二氧六环溶液(4ml)。回流4小时后,冷却到室温,加入乙醚,先用水洗4次,再用盐水洗,加无水硫酸钠干燥,真空蒸干。层析后〔固定相SiO2,淋洗液叔丁基甲基醚-己烷(10∶90)〕得到2-(4-叔-丁基苯基)环丁-1,1-二羧酸二乙酯(1.931g,58%)。
将2-(4-叔-丁苯基)环丁-1,1-二羧酸二乙酯(1.90g,5.73mmol),氯化锂(0.51g,12mmol)和水(0.11ml,6mmol)加到二甲亚砜中(10ml),并回流4小时。让混合物冷却到室温,加入己烷(50ml)和乙醚(50ml),用盐水洗,水洗5次,再用盐水洗,加无水硫酸钠干燥,并真空蒸干得2-(4-叔丁基苯基)环丁酸乙酯(0.82g,55%),供下步使用,不需纯化。在氩气氛下,将2-(4-叔-丁苯基)环丁酸乙酯(0.80g,3.08mmol)在2M乙醇钠溶液中(8ml)搅拌6小时。然后加水(2ml),并在室温下搅拌90小时。加乙醚,用2M盐酸洗涤后,再加水洗三次,用无水硫酸钠干燥,并真空蒸发得反-2-(4-叔丁基苯基)环丁羧酸(0.710g,100%)。
将草酰氯(0.33ml,3.78mmol)加到反-2-(4-叔-丁苯基)环丁羧酸(0.71g,3.08mmol)的己烷(5ml)溶液中,回流2小时。冷却,真空蒸发,加入乙醚(5ml)。将混合物冷却到0℃,加入顺-2,6-二甲基吗啉(1.40g,12.3mmol)。15分钟后,加入乙醚,用水洗三次,经无水硫酸钠干燥后,真空蒸发。层析后〔固定相SiO2,叔丁基甲基醚-己烷(25∶75)到(50∶50)〕,得到反-2-(4-叔-丁基)环丁酰-(2,6-顺-二甲基吗啉(0.71g,70%)。
在0℃,氩气氛下,将反-2-(4-叔丁苯基)环丁酰-(2,6-顺-二甲基吗啉(0.69g,2.10mmol)的干燥四氢呋喃(5ml)溶液加入正在搅拌的氢化铝锂(0.160g,4.2mmol)的干燥四氢呋喃溶液(15ml)中。在室温下搅拌4小时。在0℃下,先后加入乙酸乙酯(1ml),乙醇(2ml)和水(5ml)。混合物在乙醚和酒石酸钾钠水溶液两相间分配,分出有机相,水洗2次,再用盐水洗一次,加无水硫酸钠干燥,并真空蒸干。层析后〔固定相SiO2,淋洗液特丁甲醚-己烷(30∶70)〕得到4-〔反-2-(4-特-丁基苯基)环丁甲基〕-2,6-顺-二甲基吗啉(0.56g,85%)。
例7
混合下列配料,充分搅拌,使各个组分都被溶解,形成乳油,
按例4制备的化合物 10%
1,2-二氯乙烷 40%
十二烷基苯磺酸钙 5%
“Lubrol”L 10%
“Aromasol”H 35%
例8
用下列配料制备颗粒状的产品,首先将前面三个配料加水研磨,然后再与醋酸钠混合制备易于在液体(例如水)中分散的颗粒剂。将混合物干燥,过英国标准筛44-100目,以获得一定大小的颗粒。
按例4制备的化合物 50%
“Dispersol”T 25%
“Lubrol”APN5 1.5%
醋酸钠 23.5%
例9
将下列配料放到一起研磨,得到能够容易分散于液体里的粉剂。
按例4方法制备的化合物 45%
“Dispersol”T 5%
“Lissapol”NX 0.5%
“Cellofas”B600 2%
醋酸钠 47.5%
例10
将活性组分溶于溶剂中,将所得液体喷洒于瓷土颗粒上,溶剂挥发掉,则制得颗粒组合物。
按例4方法制得的化合物 5%
瓷土颗粒 95%
例11
将下列三种配料混合起来,制备适合用于拌种剂的组合物。
按例4方法制得的化合物 50%
矿物油 2%
瓷土 48%
例12
将活性组分同滑石粉混合,制备粉剂。
按例4方法制备的化合物 5%
滑石粉 95%
例13
将下列配料进行球磨,然后将磨碎的混合物悬浮于水中,制得Col制剂。
按例4方法制备的化合物 40%
“Dispersol”T 10%
“Lubrol”APN5 1%
水
例14
混合下列配料,研磨,使之彻底混匀制得可分散粉状制剂。
按例4制备的化合物 25%
“Aerosol”OT/B 2%
“Dispersol”A.C. 5%
瓷土 28%
硅石 40%
例15
这个例子是制备可分散粉剂。将下列配料混合于一起,放到研磨机中去研磨。
按例4方法制备的化合物 25%
“Perminal”BX 1%
“Dispersol”T 5%
聚乙烯吡咯烷酮 10%
硅石 25%
瓷土 34%
例16
混合下列配料并研磨以制备可分散粉剂。
按例2制备的化合物 25%
“Aerosol”OT/B 2%
“Dispersol”A 5%
瓷土 68%
从例7到例16中的组分比是按重量百分计算的。
在表Ⅰ、表Ⅱ和表Ⅲ中的其余化合物按例7到例16的方法来制备类似的剂型。
上述各种商品代号,解释如下:
LUBROL L:壬基酚(1mol)和环氧乙烷(13mol)的缩合物。
AROMASOL H:烷基苯的溶剂混合物
DISPERSOL T and AC:萘磺钠和甲醛的缩合物与硫酸钠的混合物
LUBROL APN5:壬基酚(1mol)和氧化萘的(5.5mol)缩合物。
CELLOFAS B600:羧甲基纤维素钠增稠剂
LISSAPOL NX:壬基酚(1mol)和环氧乙烷的(8mol)缩合物。
AEROSOL OT/B:磺基丁二酸二辛酯钠盐
PERMINAL BX:一种烷基萘磺酸钠
例17
对各个化合物进行了抗植物叶子真菌病的实验,实验方法如下:
将John Innes盆栽复合土(1号和2号)放入4cm直径的小盆里,栽种植物。将要试验的化合物放入Dispersol T的水溶液中用球磨机磨碎,或配成丙酮溶液或配成丙酮-乙醇溶液,使用前稀释到所需要的浓度。对于植物叶子病,将杀菌剂(100ppm活性组分)喷洒到簇叶上,或应用到植物在土壤里的根部。使喷洒液达到最大的泄留量,使根部浸透的最后浓度达到约40ppm活性成分(相应于干燥土壤)。若将这些杀菌剂应用到谷物上,则应加吐温-20,其最后浓度为0.05%。
在大多数实验里,在植物用病菌接种前一或两天,将这些杀菌剂应用于根部附近的土壤里或喷洒到簇叶上。对于白粉病是例外,用药前24小时用病菌接种。叶子病原体是以分散悬浮液形式喷洒到待试植物的叶子上的。喷洒了病原体后,将植物放置在适当的环境中,让它继续被感染、发展,直到它可用以做出评价为止。根据环境和病害的严重程度,从接种到评价之间的时间间隔由四天到十四天不等。
药效分以下几级:
4:无病
3:与对照组比较,病情为痕量-5%。
2:与对照组相比,病情为6-25%。
1:与对照组相比,病情为26-59%。
0:与对照组相比,病情为60-100%。
结果列于表Ⅷ。
(表Ⅷ见下页)
表Ⅷ
*对于叶上喷洒的杀菌剂为100PPm。
HGHA/jc
PP33955
87年6月4日
Claims (12)
1、具有通式(Ⅰ)的化合物及其立体异构体和酸加成盐,
其中R1和R2各自代表氢原子,卤素原子或含1到4个碳原子的烷基,R3和R4各自代表氢原子或者含1到4个碳原子的烷基,R5和R6各自或者代表含有1到4个碳原子的烷基,或者它们与邻近的氮原子共同组成一个杂环,环中还可能包括一个其它杂原子,X和Y各自代表氢原子,卤原子或者烷基、环烷基、环烷基烷基、烯基、炔基、芳基、芳烷基、烷氧基或者芳氧基,或者这样一个基团:
其中R19、R20、R21各自代表烷基、烯基、炔基、环烷基、环烷基烷基、芳基或芳烷基,通式(Ⅰ)中n的数值是1或0,Q是具有下列结构之一的桥连基团:Q1、Q2、Q3、Q4
(紧接下页)
桥连基团中的R7到R14每个分别代表氢原子、卤原子、羟基或者包含着1到4个碳原子的烷基,通式(Ⅰ)中的Z,或者是桥键(共价键,用Z0表示),或者是Z1、Z2形式的桥连基团:
其中R15到R18每个所代表的意义与R7到R14相同,但须
(i)Z为Z0时,Q不可为Q1;
(ii)在通式(Ⅰ)中,由基团Q和Z提供的形成环的碳原子总数不超过4。
2、根据权利要求1的化合物,其中R7到R18都是氢原子。
3、根据权利要求1的化合物,其中X和Y是苯基、苄基、苯氧基或者苄氧基,其中的每一个可能被下列一个或几个基团所取代:卤素(例如氟、氯、溴),C1-6烷基〔例如甲基、乙基、丙基(正或异丙基)和丁基(正、仲、异或叔丁基)〕,C1-6烷氧基(例如甲氧基、乙氧基、丙氧基和丁氧基),卤素-C1-6-烷氧基(例如三氟甲氧基)、卤素-C1-6-烷基(例如三氟甲基)、硝基、苯基和苯氧基。
4、根据权利要求1或2的化合物,其中X和Y取代基在环的2、3、4位上,尤其是4位。
5、根据权利要求1到3中之一的化合物,其中R5、R6和相邻的碳原子一起代表哌啶、吗啉、硫代吗啉、吡咯烷或哌嗪环、其中每一个都可能被下列一个或几个基团所取代:C1-4烷基、苯基或者羟基C1-4烷基。
6、根据权利要求1到4中之一的化合物,其中Y是氢,X是C1-6烷基、C3-6环烷基、C4-9环烷基烷基、C2-6链烯基、C2-6炔基、三甲硅基、三乙硅基、叔丁基二甲硅基、苯基二甲硅基或烯丙基二甲硅基。
7、根据权利要求1至6中之一的化合物,其中Y是氢,X是连在苯基环的3位或4位上的叔丁基,异丙基或三甲硅基;n是0或1;R1,R2,R3和R4是氢,Q是-CH2-,-(CH2)2,-(CH2)3-或-(CH2)4-;Z是共价键或-CH2-或-(CH2)2-;NR5R6是2,6-二甲基吗啉或哌啶。
10、一种杀真菌组合物,其中包含权利要求1至7中之一种化合物或其盐,可以有载体或稀释剂。
11、一种抗真菌的方法,其中包括将权利要求1至7中之一种化合物或其盐,或者将权利要求10的一种组合物,应用到植物上、植物种子上,或植物和种子的附近区域。
12、作为新型中间体的结构式为(Ⅱ)、(Ⅲ)、(Ⅴ)、(Ⅵ)、(Ⅶ)、(Ⅷ)、(Ⅸ)、(Ⅺ)、(Ⅻ)、(ⅩⅥ)、(ⅩⅧ)和(ⅩⅩⅤ)的化合物。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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GB8617373 | 1986-07-16 | ||
GB868617373A GB8617373D0 (en) | 1986-07-16 | 1986-07-16 | Tertiary amine compounds |
GB868622965A GB8622965D0 (en) | 1986-09-24 | 1986-09-24 | Tertiary amine compounds |
GB8622965 | 1986-09-24 |
Publications (1)
Publication Number | Publication Date |
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CN87105345A true CN87105345A (zh) | 1988-02-03 |
Family
ID=26291045
Family Applications (1)
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CN198787105345A Pending CN87105345A (zh) | 1986-07-16 | 1987-07-16 | 叔胺化合物 |
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EP (1) | EP0253501A3 (zh) |
KR (1) | KR880001621A (zh) |
CN (1) | CN87105345A (zh) |
AU (1) | AU7474987A (zh) |
DK (1) | DK371587A (zh) |
GB (1) | GB2192881A (zh) |
HU (1) | HUT44394A (zh) |
IL (1) | IL82975A0 (zh) |
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KR100330299B1 (ko) * | 1999-12-22 | 2002-03-27 | 이상환 | 밤 껍질 제거장치 |
EP2818460A1 (en) | 2013-06-24 | 2014-12-31 | ZaCh System S.p.A. | Cyclopropanation of substituted phenylacetonitriles or phenyl acetates |
CA2915773A1 (en) | 2013-06-24 | 2014-12-31 | Chiesi Farmaceutici S.P.A. | Improved process for the preparation of derivatives of 1-(2-fluoro[1,1'-biphenyl]-4-yl)-cyclopropanecarboxylic acid |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
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US2474796A (en) * | 1946-01-31 | 1949-06-28 | Wm S Merrell Co | Alkylaminoalkyl esters of alicyclyl-alicyclic carboxylic acids |
DE1214471B (de) * | 1965-01-16 | 1966-04-14 | Basf Ag | Fungizid fuer den Pflanzenschutz |
FR2270856B1 (zh) * | 1974-01-17 | 1978-07-21 | Screen | |
DE2656747C2 (de) * | 1976-12-15 | 1984-07-05 | Basf Ag, 6700 Ludwigshafen | Morpholinderivate |
US4212355A (en) * | 1978-09-11 | 1980-07-15 | Lynes, Inc. | Tubing manipulated test valve and latch assembly |
IT1113391B (it) * | 1979-05-09 | 1986-01-20 | Maggioni Farma | Derivati fenilcicloesanici ad attivita' antidepressiva |
US4399298A (en) * | 1980-02-15 | 1983-08-16 | Chisso Corporation | Carboxylic acid ester derivatives of 4-fluorophenol |
SU914547A1 (en) * | 1980-07-25 | 1982-03-23 | Inst Neftekhim Protsessov | Alkyphenylcyclohexanecarboxylic acids as base for siccatives |
DE3268611D1 (en) * | 1981-02-25 | 1986-03-06 | Hitachi Ltd | Colorless liquid crystalline compounds |
JPS58203963A (ja) * | 1982-05-20 | 1983-11-28 | Chisso Corp | トランス−4−(4′−置換フエニル)シクロヘキサンカルボン酸−4−フルオロチオフエニルエステル |
JPS5939835A (ja) * | 1982-08-27 | 1984-03-05 | Asahi Glass Co Ltd | 1−(トランス−4−アルキルシクロヘキシル)−2−{トランス−4′−(p−置換フエニル)シクロヘキシル}エタン |
JPS59141540A (ja) * | 1983-02-01 | 1984-08-14 | Chisso Corp | 三環カルボン酸エステル誘導体 |
JPS59172452A (ja) * | 1983-03-18 | 1984-09-29 | Chisso Corp | 負の誘電異方性値を持つ光学活性物質 |
GB8310141D0 (en) * | 1983-04-14 | 1983-05-18 | Wellcome Found | Naphthoquinone derivatives |
DE3321712A1 (de) * | 1983-06-16 | 1984-12-20 | Basf Ag, 6700 Ludwigshafen | 2,6-trans-dimethylmorpholinderivate und diese enthaltende fungizide und verfahren zur bekaempfung von pilzen |
DE3582728D1 (de) * | 1985-01-17 | 1991-06-06 | Ici Plc | Tertiaere aminoverbindungen. |
-
1987
- 1987-06-12 GB GB08713738A patent/GB2192881A/en not_active Withdrawn
- 1987-06-12 EP EP87305244A patent/EP0253501A3/en not_active Withdrawn
- 1987-06-24 IL IL82975A patent/IL82975A0/xx unknown
- 1987-06-26 AU AU74749/87A patent/AU7474987A/en not_active Abandoned
- 1987-07-15 HU HU873220A patent/HUT44394A/hu unknown
- 1987-07-16 DK DK371587A patent/DK371587A/da not_active Application Discontinuation
- 1987-07-16 KR KR1019870007686A patent/KR880001621A/ko not_active Application Discontinuation
- 1987-07-16 CN CN198787105345A patent/CN87105345A/zh active Pending
Also Published As
Publication number | Publication date |
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HUT44394A (en) | 1988-03-28 |
EP0253501A3 (en) | 1990-04-04 |
GB8713738D0 (en) | 1987-07-15 |
EP0253501A2 (en) | 1988-01-20 |
GB2192881A (en) | 1988-01-27 |
AU7474987A (en) | 1988-01-21 |
DK371587D0 (da) | 1987-07-16 |
KR880001621A (ko) | 1988-04-25 |
IL82975A0 (en) | 1987-12-20 |
DK371587A (da) | 1988-01-17 |
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